Synthesis and structure-activity relationships of novel 2-amino alkyl chromones and related derivatives as a site-selective ligands
Identifieur interne : 000D65 ( Istex/Corpus ); précédent : 000D64; suivant : 000D66Synthesis and structure-activity relationships of novel 2-amino alkyl chromones and related derivatives as a site-selective ligands
Auteurs : Geneviève Baziard-Mouysset ; Salouma Younes ; Youssef Labssita ; Marc Payard ; Daniel-Henri Caignard ; Marie-Claire Rettori ; Pierre Renard ; Bruno Pfeiffer ; Béatrice Guardiola-LemaitreSource :
- European Journal of Medicinal Chemistry [ 0223-5234 ] ; 1998.
English descriptors
- KwdEn :
Abstract
Abstract: Starting from a random screening showing that 2-[(4-benzylpiperazinyl)methyl] chromone was a selective and potent sigma ligand, a series of analogues were synthesized. Introduction of a substituent on the chromone moiety, replacement of methy-lenes by carbonyl groups and benzyl by aryl groups decrease the affinity for sigma sites. The result obtained after introduction of various substituents on the aromatic part of the benzyl is strictly depending on the size and on the position of these substituents. Stretching of the carbon chain between the phenyl and the piperazine does not strongly modify the affinity. 2-[4-(4′-methoxy benzyl)-1-piperazinyl methyl] chromone has been tested in behavioral tests that permit to believe that such derivatives could be interesting for the treatment of psychosis.
Url:
DOI: 10.1016/S0223-5234(98)80001-9
Links to Exploration step
ISTEX:757D0ADA964638FA3C72A52EFA1A92FB2F265FC5Le document en format XML
<record><TEI wicri:istexFullTextTei="biblStruct"><teiHeader><fileDesc><titleStmt><title xml:lang="en">Synthesis and structure-activity relationships of novel 2-amino alkyl chromones and related derivatives as a site-selective ligands</title><author><name sortKey="Baziard Mouysset, Genevieve" sort="Baziard Mouysset, Genevieve" uniqKey="Baziard Mouysset G" first="Geneviève" last="Baziard-Mouysset">Geneviève Baziard-Mouysset</name><affiliation><mods:affiliation>Laboratoire de Chimie Pharmaceutique, Faculté de Pharmacie, 35 Chemin des Maraichers, 31062 Toulouse, France</mods:affiliation></affiliation></author><author><name sortKey="Younes, Salouma" sort="Younes, Salouma" uniqKey="Younes S" first="Salouma" last="Younes">Salouma Younes</name><affiliation><mods:affiliation>Laboratoire de Chimie Pharmaceutique, Faculté de Pharmacie, 35 Chemin des Maraichers, 31062 Toulouse, France</mods:affiliation></affiliation></author><author><name sortKey="Labssita, Youssef" sort="Labssita, Youssef" uniqKey="Labssita Y" first="Youssef" last="Labssita">Youssef Labssita</name><affiliation><mods:affiliation>Laboratoire de Chimie Pharmaceutique, Faculté de Pharmacie, 35 Chemin des Maraichers, 31062 Toulouse, France</mods:affiliation></affiliation></author><author><name sortKey="Payard, Marc" sort="Payard, Marc" uniqKey="Payard M" first="Marc" last="Payard">Marc Payard</name><affiliation><mods:affiliation>Laboratoire de Chimie Pharmaceutique, Faculté de Pharmacie, 35 Chemin des Maraichers, 31062 Toulouse, France</mods:affiliation></affiliation></author><author><name sortKey="Caignard, Daniel Henri" sort="Caignard, Daniel Henri" uniqKey="Caignard D" first="Daniel-Henri" last="Caignard">Daniel-Henri Caignard</name><affiliation><mods:affiliation>Institut de Recherches International Servier, 1 Rue Carle Hébert, 92415 Courbevoie Cedex, France</mods:affiliation></affiliation><affiliation><mods:affiliation>Correspondence and reprints.</mods:affiliation></affiliation></author><author><name sortKey="Rettori, Marie Claire" sort="Rettori, Marie Claire" uniqKey="Rettori M" first="Marie-Claire" last="Rettori">Marie-Claire Rettori</name><affiliation><mods:affiliation>Institut de Recherches International Servier, 1 Rue Carle Hébert, 92415 Courbevoie Cedex, France</mods:affiliation></affiliation></author><author><name sortKey="Renard, Pierre" sort="Renard, Pierre" uniqKey="Renard P" first="Pierre" last="Renard">Pierre Renard</name><affiliation><mods:affiliation>Institut de Recherches International Servier, 1 Rue Carle Hébert, 92415 Courbevoie Cedex, France</mods:affiliation></affiliation></author><author><name sortKey="Pfeiffer, Bruno" sort="Pfeiffer, Bruno" uniqKey="Pfeiffer B" first="Bruno" last="Pfeiffer">Bruno Pfeiffer</name><affiliation><mods:affiliation>Institut de Recherches International Servier, 1 Rue Carle Hébert, 92415 Courbevoie Cedex, France</mods:affiliation></affiliation></author><author><name sortKey="Guardiola Lemaitre, Beatrice" sort="Guardiola Lemaitre, Beatrice" uniqKey="Guardiola Lemaitre B" first="Béatrice" last="Guardiola-Lemaitre">Béatrice Guardiola-Lemaitre</name><affiliation><mods:affiliation>Institut de Recherches International Servier, 1 Rue Carle Hébert, 92415 Courbevoie Cedex, France</mods:affiliation></affiliation></author></titleStmt><publicationStmt><idno type="wicri:source">ISTEX</idno><idno type="RBID">ISTEX:757D0ADA964638FA3C72A52EFA1A92FB2F265FC5</idno><date when="1998" year="1998">1998</date><idno type="doi">10.1016/S0223-5234(98)80001-9</idno><idno type="url">https://api.istex.fr/document/757D0ADA964638FA3C72A52EFA1A92FB2F265FC5/fulltext/pdf</idno><idno type="wicri:Area/Istex/Corpus">000D65</idno><idno type="wicri:explorRef" wicri:stream="Istex" wicri:step="Corpus" wicri:corpus="ISTEX">000D65</idno></publicationStmt><sourceDesc><biblStruct><analytic><title level="a" type="main" xml:lang="en">Synthesis and structure-activity relationships of novel 2-amino alkyl chromones and related derivatives as a site-selective ligands</title><author><name sortKey="Baziard Mouysset, Genevieve" sort="Baziard Mouysset, Genevieve" uniqKey="Baziard Mouysset G" first="Geneviève" last="Baziard-Mouysset">Geneviève Baziard-Mouysset</name><affiliation><mods:affiliation>Laboratoire de Chimie Pharmaceutique, Faculté de Pharmacie, 35 Chemin des Maraichers, 31062 Toulouse, France</mods:affiliation></affiliation></author><author><name sortKey="Younes, Salouma" sort="Younes, Salouma" uniqKey="Younes S" first="Salouma" last="Younes">Salouma Younes</name><affiliation><mods:affiliation>Laboratoire de Chimie Pharmaceutique, Faculté de Pharmacie, 35 Chemin des Maraichers, 31062 Toulouse, France</mods:affiliation></affiliation></author><author><name sortKey="Labssita, Youssef" sort="Labssita, Youssef" uniqKey="Labssita Y" first="Youssef" last="Labssita">Youssef Labssita</name><affiliation><mods:affiliation>Laboratoire de Chimie Pharmaceutique, Faculté de Pharmacie, 35 Chemin des Maraichers, 31062 Toulouse, France</mods:affiliation></affiliation></author><author><name sortKey="Payard, Marc" sort="Payard, Marc" uniqKey="Payard M" first="Marc" last="Payard">Marc Payard</name><affiliation><mods:affiliation>Laboratoire de Chimie Pharmaceutique, Faculté de Pharmacie, 35 Chemin des Maraichers, 31062 Toulouse, France</mods:affiliation></affiliation></author><author><name sortKey="Caignard, Daniel Henri" sort="Caignard, Daniel Henri" uniqKey="Caignard D" first="Daniel-Henri" last="Caignard">Daniel-Henri Caignard</name><affiliation><mods:affiliation>Institut de Recherches International Servier, 1 Rue Carle Hébert, 92415 Courbevoie Cedex, France</mods:affiliation></affiliation><affiliation><mods:affiliation>Correspondence and reprints.</mods:affiliation></affiliation></author><author><name sortKey="Rettori, Marie Claire" sort="Rettori, Marie Claire" uniqKey="Rettori M" first="Marie-Claire" last="Rettori">Marie-Claire Rettori</name><affiliation><mods:affiliation>Institut de Recherches International Servier, 1 Rue Carle Hébert, 92415 Courbevoie Cedex, France</mods:affiliation></affiliation></author><author><name sortKey="Renard, Pierre" sort="Renard, Pierre" uniqKey="Renard P" first="Pierre" last="Renard">Pierre Renard</name><affiliation><mods:affiliation>Institut de Recherches International Servier, 1 Rue Carle Hébert, 92415 Courbevoie Cedex, France</mods:affiliation></affiliation></author><author><name sortKey="Pfeiffer, Bruno" sort="Pfeiffer, Bruno" uniqKey="Pfeiffer B" first="Bruno" last="Pfeiffer">Bruno Pfeiffer</name><affiliation><mods:affiliation>Institut de Recherches International Servier, 1 Rue Carle Hébert, 92415 Courbevoie Cedex, France</mods:affiliation></affiliation></author><author><name sortKey="Guardiola Lemaitre, Beatrice" sort="Guardiola Lemaitre, Beatrice" uniqKey="Guardiola Lemaitre B" first="Béatrice" last="Guardiola-Lemaitre">Béatrice Guardiola-Lemaitre</name><affiliation><mods:affiliation>Institut de Recherches International Servier, 1 Rue Carle Hébert, 92415 Courbevoie Cedex, France</mods:affiliation></affiliation></author></analytic><monogr></monogr><series><title level="j">European Journal of Medicinal Chemistry</title><title level="j" type="abbrev">EJMECH</title><idno type="ISSN">0223-5234</idno><imprint><publisher>ELSEVIER</publisher><date type="published" when="1998">1998</date><biblScope unit="volume">33</biblScope><biblScope unit="issue">5</biblScope><biblScope unit="page" from="339">339</biblScope><biblScope unit="page" to="347">347</biblScope></imprint><idno type="ISSN">0223-5234</idno></series><idno type="istex">757D0ADA964638FA3C72A52EFA1A92FB2F265FC5</idno><idno type="DOI">10.1016/S0223-5234(98)80001-9</idno><idno type="PII">S0223-5234(98)80001-9</idno><idno type="ArticleID">98800019</idno></biblStruct></sourceDesc><seriesStmt><idno type="ISSN">0223-5234</idno></seriesStmt></fileDesc><profileDesc><textClass><keywords scheme="KwdEn" xml:lang="en"><term>benzylpiperazine</term><term>chromone</term><term>psychosis</term><term>sigma ligand</term></keywords></textClass><langUsage><language ident="en">en</language></langUsage></profileDesc></teiHeader><front><div type="abstract" xml:lang="en">Abstract: Starting from a random screening showing that 2-[(4-benzylpiperazinyl)methyl] chromone was a selective and potent sigma ligand, a series of analogues were synthesized. Introduction of a substituent on the chromone moiety, replacement of methy-lenes by carbonyl groups and benzyl by aryl groups decrease the affinity for sigma sites. The result obtained after introduction of various substituents on the aromatic part of the benzyl is strictly depending on the size and on the position of these substituents. Stretching of the carbon chain between the phenyl and the piperazine does not strongly modify the affinity. 2-[4-(4′-methoxy benzyl)-1-piperazinyl methyl] chromone has been tested in behavioral tests that permit to believe that such derivatives could be interesting for the treatment of psychosis.</div></front></TEI><istex><corpusName>elsevier</corpusName><author><json:item><name>Geneviève Baziard-Mouysset</name><affiliations><json:string>Laboratoire de Chimie Pharmaceutique, Faculté de Pharmacie, 35 Chemin des Maraichers, 31062 Toulouse, France</json:string></affiliations></json:item><json:item><name>Salouma Younes</name><affiliations><json:string>Laboratoire de Chimie Pharmaceutique, Faculté de Pharmacie, 35 Chemin des Maraichers, 31062 Toulouse, France</json:string></affiliations></json:item><json:item><name>Youssef Labssita</name><affiliations><json:string>Laboratoire de Chimie Pharmaceutique, Faculté de Pharmacie, 35 Chemin des Maraichers, 31062 Toulouse, France</json:string></affiliations></json:item><json:item><name>Marc Payard</name><affiliations><json:string>Laboratoire de Chimie Pharmaceutique, Faculté de Pharmacie, 35 Chemin des Maraichers, 31062 Toulouse, France</json:string></affiliations></json:item><json:item><name>Daniel-Henri Caignard</name><affiliations><json:string>Institut de Recherches International Servier, 1 Rue Carle Hébert, 92415 Courbevoie Cedex, France</json:string><json:string>Correspondence and reprints.</json:string></affiliations></json:item><json:item><name>Marie-Claire Rettori</name><affiliations><json:string>Institut de Recherches International Servier, 1 Rue Carle Hébert, 92415 Courbevoie Cedex, France</json:string></affiliations></json:item><json:item><name>Pierre Renard</name><affiliations><json:string>Institut de Recherches International Servier, 1 Rue Carle Hébert, 92415 Courbevoie Cedex, France</json:string></affiliations></json:item><json:item><name>Bruno Pfeiffer</name><affiliations><json:string>Institut de Recherches International Servier, 1 Rue Carle Hébert, 92415 Courbevoie Cedex, France</json:string></affiliations></json:item><json:item><name>Béatrice Guardiola-Lemaitre</name><affiliations><json:string>Institut de Recherches International Servier, 1 Rue Carle Hébert, 92415 Courbevoie Cedex, France</json:string></affiliations></json:item></author><subject><json:item><lang><json:string>eng</json:string></lang><value>sigma ligand</value></json:item><json:item><lang><json:string>eng</json:string></lang><value>chromone</value></json:item><json:item><lang><json:string>eng</json:string></lang><value>benzylpiperazine</value></json:item><json:item><lang><json:string>eng</json:string></lang><value>psychosis</value></json:item></subject><articleId><json:string>98800019</json:string></articleId><language><json:string>eng</json:string></language><originalGenre><json:string>Full-length article</json:string></originalGenre><abstract>Abstract: Starting from a random screening showing that 2-[(4-benzylpiperazinyl)methyl] chromone was a selective and potent sigma ligand, a series of analogues were synthesized. Introduction of a substituent on the chromone moiety, replacement of methy-lenes by carbonyl groups and benzyl by aryl groups decrease the affinity for sigma sites. The result obtained after introduction of various substituents on the aromatic part of the benzyl is strictly depending on the size and on the position of these substituents. Stretching of the carbon chain between the phenyl and the piperazine does not strongly modify the affinity. 2-[4-(4′-methoxy benzyl)-1-piperazinyl methyl] chromone has been tested in behavioral tests that permit to believe that such derivatives could be interesting for the treatment of psychosis.</abstract><qualityIndicators><score>5.816</score><pdfVersion>1.3</pdfVersion><pdfPageSize>612 x 792 pts (letter)</pdfPageSize><refBibsNative>true</refBibsNative><keywordCount>4</keywordCount><abstractCharCount>815</abstractCharCount><pdfWordCount>4400</pdfWordCount><pdfCharCount>29228</pdfCharCount><pdfPageCount>9</pdfPageCount><abstractWordCount>118</abstractWordCount></qualityIndicators><title>Synthesis and structure-activity relationships of novel 2-amino alkyl chromones and related derivatives as a site-selective ligands</title><pii><json:string>S0223-5234(98)80001-9</json:string></pii><refBibs><json:item><host><volume>197</volume><pages><last>532</last><first>517</first></pages><author></author><title>J. Pharmacol. Exp. Ther.</title></host></json:item><json:item><host><volume>12</volume><pages><last>374</last><first>353</first></pages><author></author><title>Clin. Neuropharmacol.</title></host></json:item><json:item><host><volume>42</volume><pages><last>402</last><first>355</first></pages><author></author><title>Pharmacol. Rev.</title></host></json:item><json:item><host><volume>13</volume><pages><last>86</last><first>85</first></pages><author></author><title>Trends Pharmacol. Sci.</title></host></json:item><json:item><host><volume>35</volume><pages><last>5</last><first>1</first></pages><author></author><title>J. Mol. Pharmacol.</title></host></json:item><json:item><host><volume>206</volume><pages><last>269</last><first>261</first></pages><author></author><title>Eur. J. Pharmacol.</title></host></json:item><json:item><host><volume>527</volume><pages><last>253</last><first>244</first></pages><author></author><title>Brain Res.</title></host></json:item><json:item><host><volume>581</volume><pages><last>38</last><first>33</first></pages><author></author><title>Brain Res.</title></host></json:item><json:item><host><volume>37</volume><pages><last>4217</last><first>4109</first></pages><author></author><title>J. Med. Chem.</title></host></json:item><json:item><host><volume>5</volume><pages><last>393</last><first>387</first></pages><author></author><title>Drug Dev. Res.</title></host></json:item><json:item><host><volume>35</volume><pages><last>1535</last><first>1526</first></pages><author></author><title>J. Med. Chem.</title></host></json:item><json:item><host><volume>35</volume><pages><last>1535</last><first>1526</first></pages><author></author><title>J. Med. Chem.</title></host></json:item><json:item><host><volume>25</volume><pages><last>269</last><first>259</first></pages><author></author><title>Neuroscience</title></host></json:item><json:item><host><volume>36</volume><pages><last>155</last><first>151</first></pages><author></author><title>Pharmacol. Biochem. Behav.</title></host></json:item><json:item><host><volume>124</volume><pages><last>1172</last><first>1160</first></pages><author></author><title>Endocrinology</title></host></json:item><json:item><host><volume>148</volume><pages><last>470</last><first>467</first></pages><author></author><title>Eur. J. Pharmacol.</title></host></json:item><json:item><host><volume>247</volume><pages><last>1119</last><first>1114</first></pages><author></author><title>J. Pharmacol. Exp. Ther.</title></host></json:item><json:item><host><volume>253</volume><pages><last>129</last><first>124</first></pages><author></author><title>J. Pharmacol. Exp. Ther.</title></host></json:item><json:item><host><volume>256</volume><pages><last>524</last><first>519</first></pages><author></author><title>J. Pharmacol. Exp. Ther.</title></host></json:item><json:item><host><volume>240</volume><pages><last>221</last><first>219</first></pages><author></author><title>Science</title></host></json:item><json:item><host><volume>1</volume><pages><last>15</last><first>7</first></pages><author></author><title>J. Neuropsychiatry</title></host></json:item><json:item><host><volume>28</volume><pages><last>10</last><first>1</first></pages><author></author><title>Ann. Rep. Med. Chem.</title></host></json:item><json:item><host><volume>546</volume><pages><last>82</last><first>79</first></pages><author></author><title>Brain Res.</title></host></json:item><json:item><host><volume>51</volume><pages><last>1149</last><first>1145</first></pages><author></author><title>Life Sci.</title></host></json:item><json:item><host><volume>546</volume><pages><last>286</last><first>282</first></pages><author></author><title>Brain Res.</title></host></json:item><json:item><host><volume>7</volume><pages><last>5</last><first>1</first></pages><author></author><title>Neurotransmissions</title></host></json:item><json:item><host><volume>272</volume><pages><last>230</last><first>224</first></pages><author></author><title>J. Pharmacol Exp. Ther.</title></host></json:item><json:item><host><volume>2</volume><pages><last>166</last><first>162</first></pages><author></author><title>J. Pharm. Belg.</title></host></json:item><json:item><host><volume>25 B</volume><pages><last>389</last><first>384</first></pages><issue>4</issue><author></author><title>Ind. J. Chem. Sect. B.</title></host></json:item><json:item><host><volume>34</volume><pages><last>86</last><first>71</first></pages><issue>2</issue><author></author><title>Taiwan Yao H. Tsa Chich.</title></host></json:item><json:item><host><volume>15</volume><pages><last>867</last><first>865</first></pages><issue>8</issue><author></author><title>J. Med. Chem.</title></host></json:item><json:item><host><volume>137</volume><pages><first>137</first></pages><author></author><title>Chem. Abstr. 79</title></host></json:item><json:item><host><volume>137</volume><pages><first>1310</first></pages><author></author><title>Chem. Abstr. 79</title></host></json:item><json:item><host><volume>33</volume><pages><last>3110</last><first>3100</first></pages><author></author><title>J. Med. Chem.</title></host></json:item><json:item><host><volume>7–8</volume><pages><first>2392</first></pages><author></author><title>Bull. Soc. Chim. Fr.</title></host></json:item><json:item><host><volume>23</volume><pages><last>202</last><first>199</first></pages><author></author><title>Eur. J. Med. Chem.</title></host></json:item><json:item><host><volume>20</volume><pages><last>120</last><first>117</first></pages><author></author><title>Eur. J. Med. Chem.</title></host></json:item><json:item><host><volume>22</volume><pages><last>544</last><first>539</first></pages><author></author><title>Eur. J. Med. Chem.</title></host></json:item><json:item><host><volume>193</volume><pages><last>27</last><first>21</first></pages><author></author><title>Eur. J. Pharmacol.</title></host></json:item><json:item><host><volume>118</volume><pages><last>23</last><first>13</first></pages><author></author><title>Eur. J. Pharmacol.</title></host></json:item><json:item><host><volume>34</volume><pages><last>2259</last><first>2251</first></pages><author></author><title>Biochem. Pharmacol.</title></host></json:item><json:item><host><volume>227</volume><pages><last>378</last><first>371</first></pages><author></author><title>Eur. J. Pharmacol.</title></host></json:item><json:item><author><json:item><name>E. Weber</name></json:item><json:item><name>M. Sonders</name></json:item><json:item><name>M. Quarum</name></json:item><json:item><name>S. McLean</name></json:item><json:item><name>S. Pou</name></json:item><json:item><name>JFW. Keana</name></json:item></author><host><author></author><title>19</title></host><serie><author></author><title>19</title></serie><title>Proc. Nat. Acad. Sci USA.</title></json:item><json:item><host><volume>261</volume><pages><last>130</last><first>123</first></pages><author></author><title>J. Pharmacol. Exp. Ther.</title></host></json:item><json:item><host><volume>179</volume><pages><last>445</last><first>441</first></pages><author></author><title>Eur. J. Pharmacol.</title></host></json:item><json:item><host><volume>123</volume><pages><last>111</last><first>89</first></pages><author></author><title>Brain Research</title></host></json:item></refBibs><genre><json:string>research-article</json:string></genre><serie><language><json:string>unknown</json:string></language><title>19</title></serie><host><volume>33</volume><pii><json:string>S0223-5234(00)X0166-3</json:string></pii><pages><last>347</last><first>339</first></pages><issn><json:string>0223-5234</json:string></issn><issue>5</issue><genre><json:string>journal</json:string></genre><language><json:string>unknown</json:string></language><title>European Journal of Medicinal Chemistry</title><publicationDate>1998</publicationDate></host><categories><wos><json:string>science</json:string><json:string>chemistry, medicinal</json:string></wos><scienceMetrix><json:string>natural sciences</json:string><json:string>chemistry</json:string><json:string>medicinal & biomolecular chemistry</json:string></scienceMetrix></categories><publicationDate>1998</publicationDate><copyrightDate>1998</copyrightDate><doi><json:string>10.1016/S0223-5234(98)80001-9</json:string></doi><id>757D0ADA964638FA3C72A52EFA1A92FB2F265FC5</id><score>0.12538221</score><fulltext><json:item><extension>pdf</extension><original>true</original><mimetype>application/pdf</mimetype><uri>https://api.istex.fr/document/757D0ADA964638FA3C72A52EFA1A92FB2F265FC5/fulltext/pdf</uri></json:item><json:item><extension>zip</extension><original>false</original><mimetype>application/zip</mimetype><uri>https://api.istex.fr/document/757D0ADA964638FA3C72A52EFA1A92FB2F265FC5/fulltext/zip</uri></json:item><istex:fulltextTEI uri="https://api.istex.fr/document/757D0ADA964638FA3C72A52EFA1A92FB2F265FC5/fulltext/tei"><teiHeader><fileDesc><titleStmt><title level="a" type="main" xml:lang="en">Synthesis and structure-activity relationships of novel 2-amino alkyl chromones and related derivatives as a site-selective ligands</title></titleStmt><publicationStmt><authority>ISTEX</authority><publisher>ELSEVIER</publisher><availability><p>©1998 Elsevier, Paris</p></availability><date>1998</date></publicationStmt><sourceDesc><biblStruct type="inbook"><analytic><title level="a" type="main" xml:lang="en">Synthesis and structure-activity relationships of novel 2-amino alkyl chromones and related derivatives as a site-selective ligands</title><author xml:id="author-1"><persName><forename type="first">Geneviève</forename><surname>Baziard-Mouysset</surname></persName><affiliation>Laboratoire de Chimie Pharmaceutique, Faculté de Pharmacie, 35 Chemin des Maraichers, 31062 Toulouse, France</affiliation></author><author xml:id="author-2"><persName><forename type="first">Salouma</forename><surname>Younes</surname></persName><affiliation>Laboratoire de Chimie Pharmaceutique, Faculté de Pharmacie, 35 Chemin des Maraichers, 31062 Toulouse, France</affiliation></author><author xml:id="author-3"><persName><forename type="first">Youssef</forename><surname>Labssita</surname></persName><affiliation>Laboratoire de Chimie Pharmaceutique, Faculté de Pharmacie, 35 Chemin des Maraichers, 31062 Toulouse, France</affiliation></author><author xml:id="author-4"><persName><forename type="first">Marc</forename><surname>Payard</surname></persName><affiliation>Laboratoire de Chimie Pharmaceutique, Faculté de Pharmacie, 35 Chemin des Maraichers, 31062 Toulouse, France</affiliation></author><author xml:id="author-5"><persName><forename type="first">Daniel-Henri</forename><surname>Caignard</surname></persName><affiliation>Institut de Recherches International Servier, 1 Rue Carle Hébert, 92415 Courbevoie Cedex, France</affiliation><affiliation>Correspondence and reprints.</affiliation></author><author xml:id="author-6"><persName><forename type="first">Marie-Claire</forename><surname>Rettori</surname></persName><affiliation>Institut de Recherches International Servier, 1 Rue Carle Hébert, 92415 Courbevoie Cedex, France</affiliation></author><author xml:id="author-7"><persName><forename type="first">Pierre</forename><surname>Renard</surname></persName><affiliation>Institut de Recherches International Servier, 1 Rue Carle Hébert, 92415 Courbevoie Cedex, France</affiliation></author><author xml:id="author-8"><persName><forename type="first">Bruno</forename><surname>Pfeiffer</surname></persName><affiliation>Institut de Recherches International Servier, 1 Rue Carle Hébert, 92415 Courbevoie Cedex, France</affiliation></author><author xml:id="author-9"><persName><forename type="first">Béatrice</forename><surname>Guardiola-Lemaitre</surname></persName><affiliation>Institut de Recherches International Servier, 1 Rue Carle Hébert, 92415 Courbevoie Cedex, France</affiliation></author></analytic><monogr><title level="j">European Journal of Medicinal Chemistry</title><title level="j" type="abbrev">EJMECH</title><idno type="pISSN">0223-5234</idno><idno type="PII">S0223-5234(00)X0166-3</idno><imprint><publisher>ELSEVIER</publisher><date type="published" when="1998"></date><biblScope unit="volume">33</biblScope><biblScope unit="issue">5</biblScope><biblScope unit="page" from="339">339</biblScope><biblScope unit="page" to="347">347</biblScope></imprint></monogr><idno type="istex">757D0ADA964638FA3C72A52EFA1A92FB2F265FC5</idno><idno type="DOI">10.1016/S0223-5234(98)80001-9</idno><idno type="PII">S0223-5234(98)80001-9</idno><idno type="ArticleID">98800019</idno></biblStruct></sourceDesc></fileDesc><profileDesc><creation><date>1998</date></creation><langUsage><language ident="en">en</language></langUsage><abstract xml:lang="en"><p>Abstract: Starting from a random screening showing that 2-[(4-benzylpiperazinyl)methyl] chromone was a selective and potent sigma ligand, a series of analogues were synthesized. Introduction of a substituent on the chromone moiety, replacement of methy-lenes by carbonyl groups and benzyl by aryl groups decrease the affinity for sigma sites. The result obtained after introduction of various substituents on the aromatic part of the benzyl is strictly depending on the size and on the position of these substituents. Stretching of the carbon chain between the phenyl and the piperazine does not strongly modify the affinity. 2-[4-(4′-methoxy benzyl)-1-piperazinyl methyl] chromone has been tested in behavioral tests that permit to believe that such derivatives could be interesting for the treatment of psychosis.</p></abstract><textClass xml:lang="en"><keywords scheme="keyword"><list><item><term>sigma ligand</term></item><item><term>chromone</term></item><item><term>benzylpiperazine</term></item><item><term>psychosis</term></item></list></keywords></textClass></profileDesc><revisionDesc><change when="1998">Published</change></revisionDesc></teiHeader></istex:fulltextTEI><json:item><extension>txt</extension><original>false</original><mimetype>text/plain</mimetype><uri>https://api.istex.fr/document/757D0ADA964638FA3C72A52EFA1A92FB2F265FC5/fulltext/txt</uri></json:item></fulltext><metadata><istex:metadataXml wicri:clean="Elsevier doc found" wicri:toSee="Elsevier, no converted or simple article"><istex:xmlDeclaration>version="1.0" encoding="utf-8"</istex:xmlDeclaration><istex:docType PUBLIC="-//ES//DTD journal article DTD version 5.0.1//EN//XML" URI="art501.dtd" name="istex:docType"></istex:docType><istex:document><article version="5.0" xml:lang="en" docsubtype="fla"><item-info><jid>EJMECH</jid><aid>98800019</aid><ce:pii>S0223-5234(98)80001-9</ce:pii><ce:doi>10.1016/S0223-5234(98)80001-9</ce:doi><ce:copyright type="unknown" year="1998">Elsevier, Paris</ce:copyright></item-info><head><ce:title>Synthesis and structure-activity relationships of novel 2-amino alkyl chromones and related derivatives as a site-selective ligands</ce:title><ce:author-group><ce:author><ce:given-name>Geneviève</ce:given-name><ce:surname>Baziard-Mouysset</ce:surname><ce:cross-ref refid="aff1"><ce:sup>a</ce:sup></ce:cross-ref></ce:author><ce:author><ce:given-name>Salouma</ce:given-name><ce:surname>Younes</ce:surname><ce:cross-ref refid="aff1"><ce:sup>a</ce:sup></ce:cross-ref></ce:author><ce:author><ce:given-name>Youssef</ce:given-name><ce:surname>Labssita</ce:surname><ce:cross-ref refid="aff1"><ce:sup>a</ce:sup></ce:cross-ref></ce:author><ce:author><ce:given-name>Marc</ce:given-name><ce:surname>Payard</ce:surname><ce:cross-ref refid="aff1"><ce:sup>a</ce:sup></ce:cross-ref></ce:author><ce:author><ce:given-name>Daniel-Henri</ce:given-name><ce:surname>Caignard</ce:surname><ce:cross-ref refid="aff2"><ce:sup>b</ce:sup></ce:cross-ref><ce:cross-ref refid="cor1"><ce:sup>*</ce:sup></ce:cross-ref></ce:author><ce:author><ce:given-name>Marie-Claire</ce:given-name><ce:surname>Rettori</ce:surname><ce:cross-ref refid="aff2"><ce:sup>b</ce:sup></ce:cross-ref></ce:author><ce:author><ce:given-name>Pierre</ce:given-name><ce:surname>Renard</ce:surname><ce:cross-ref refid="aff2"><ce:sup>b</ce:sup></ce:cross-ref></ce:author><ce:author><ce:given-name>Bruno</ce:given-name><ce:surname>Pfeiffer</ce:surname><ce:cross-ref refid="aff2"><ce:sup>b</ce:sup></ce:cross-ref></ce:author><ce:author><ce:given-name>Béatrice</ce:given-name><ce:surname>Guardiola-Lemaitre</ce:surname><ce:cross-ref refid="aff2"><ce:sup>b</ce:sup></ce:cross-ref></ce:author><ce:affiliation id="aff1"><ce:label>a</ce:label><ce:textfn>Laboratoire de Chimie Pharmaceutique, Faculté de Pharmacie, 35 Chemin des Maraichers, 31062 Toulouse, France</ce:textfn></ce:affiliation><ce:affiliation id="aff2"><ce:label>b</ce:label><ce:textfn>Institut de Recherches International Servier, 1 Rue Carle Hébert, 92415 Courbevoie Cedex, France</ce:textfn></ce:affiliation><ce:correspondence id="cor1"><ce:label>*</ce:label><ce:text>Correspondence and reprints.</ce:text></ce:correspondence></ce:author-group><ce:date-received day="9" month="7" year="1997"></ce:date-received><ce:date-accepted day="17" month="10" year="1997"></ce:date-accepted><ce:abstract id="ab1" class="author" xml:lang="en"><ce:section-title>Abstract</ce:section-title><ce:abstract-sec><ce:simple-para>Starting from a random screening showing that 2-[(4-benzylpiperazinyl)methyl] chromone was a selective and potent sigma ligand, a series of analogues were synthesized. Introduction of a substituent on the chromone moiety, replacement of methy-lenes by carbonyl groups and benzyl by aryl groups decrease the affinity for sigma sites. The result obtained after introduction of various substituents on the aromatic part of the benzyl is strictly depending on the size and on the position of these substituents. Stretching of the carbon chain between the phenyl and the piperazine does not strongly modify the affinity. 2-[4-(4′-methoxy benzyl)-1-piperazinyl methyl] chromone has been tested in behavioral tests that permit to believe that such derivatives could be interesting for the treatment of psychosis.</ce:simple-para></ce:abstract-sec></ce:abstract><ce:keywords class="keyword" xml:lang="en"><ce:keyword><ce:text>sigma ligand</ce:text></ce:keyword><ce:keyword><ce:text>chromone</ce:text></ce:keyword><ce:keyword><ce:text>benzylpiperazine</ce:text></ce:keyword><ce:keyword><ce:text>psychosis</ce:text></ce:keyword></ce:keywords></head><tail><ce:bibliography><ce:section-title>References</ce:section-title><ce:bibliography-sec><ce:bib-reference id="bib1"><ce:label>[1]</ce:label><sb:reference><sb:contribution langtype="en"><sb:authors><sb:author><ce:surname>Martin</ce:surname><ce:given-name>W.R.</ce:given-name></sb:author><sb:author><ce:surname>Eades</ce:surname><ce:given-name>C.G.</ce:given-name></sb:author><sb:author><ce:surname>Thompson</ce:surname><ce:given-name>J.A.</ce:given-name></sb:author><sb:author><ce:surname>Huppler</ce:surname><ce:given-name>R.E.</ce:given-name></sb:author><sb:author><ce:surname>Gilbert</ce:surname><ce:given-name>P.E.</ce:given-name></sb:author></sb:authors></sb:contribution><sb:host><sb:issue><sb:series><sb:title><sb:maintitle>J. Pharmacol. Exp. Ther.</sb:maintitle></sb:title><sb:volume-nr>197</sb:volume-nr></sb:series><sb:date>1976</sb:date></sb:issue><sb:pages><sb:first-page>517</sb:first-page><sb:last-page>532</sb:last-page></sb:pages></sb:host></sb:reference></ce:bib-reference><ce:bib-reference id="bib2"><ce:label>[2]</ce:label><sb:reference><sb:contribution langtype="en"><sb:authors><sb:author><ce:surname>Junien</ce:surname><ce:given-name>J.L.</ce:given-name></sb:author><sb:author><ce:surname>Leonard</ce:surname><ce:given-name>B.E.</ce:given-name></sb:author></sb:authors></sb:contribution><sb:host><sb:issue><sb:series><sb:title><sb:maintitle>Clin. Neuropharmacol.</sb:maintitle></sb:title><sb:volume-nr>12</sb:volume-nr></sb:series><sb:date>1989</sb:date></sb:issue><sb:pages><sb:first-page>353</sb:first-page><sb:last-page>374</sb:last-page></sb:pages></sb:host></sb:reference></ce:bib-reference><ce:bib-reference id="bib3"><ce:label>[3]</ce:label><sb:reference><sb:contribution langtype="en"><sb:authors><sb:author><ce:surname>Walker</ce:surname><ce:given-name>J.M.</ce:given-name></sb:author><sb:author><ce:surname>Bowen</ce:surname><ce:given-name>W.D.</ce:given-name></sb:author><sb:author><ce:surname>Walker</ce:surname><ce:given-name>F.O.</ce:given-name></sb:author><sb:author><ce:surname>Matsumoto</ce:surname><ce:given-name>R.R.</ce:given-name></sb:author><sb:author><ce:surname>De Costa</ce:surname><ce:given-name>B.R.</ce:given-name></sb:author><sb:author><ce:surname>Rice</ce:surname><ce:given-name>K.C.</ce:given-name></sb:author></sb:authors></sb:contribution><sb:host><sb:issue><sb:series><sb:title><sb:maintitle>Pharmacol. Rev.</sb:maintitle></sb:title><sb:volume-nr>42</sb:volume-nr></sb:series><sb:date>1990</sb:date></sb:issue><sb:pages><sb:first-page>355</sb:first-page><sb:last-page>402</sb:last-page></sb:pages></sb:host></sb:reference></ce:bib-reference><ce:bib-reference id="bib4"><ce:label>[4]</ce:label><sb:reference><sb:contribution langtype="en"><sb:authors><sb:author><ce:surname>Quirion</ce:surname><ce:given-name>R.</ce:given-name></sb:author><sb:author><ce:surname>Bowen</ce:surname><ce:given-name>W.D.</ce:given-name></sb:author><sb:author><ce:surname>Itzhak</ce:surname><ce:given-name>Y.</ce:given-name></sb:author><sb:author><ce:surname>Junien</ce:surname><ce:given-name>J.L.</ce:given-name></sb:author><sb:author><ce:surname>Musacchio</ce:surname><ce:given-name>J.M.</ce:given-name></sb:author><sb:author><ce:surname>Rothman</ce:surname><ce:given-name>R.B.</ce:given-name></sb:author><sb:author><ce:surname>Su</ce:surname><ce:given-name>T.P.</ce:given-name></sb:author><sb:author><ce:surname>Tam</ce:surname><ce:given-name>S.W.</ce:given-name></sb:author><sb:author><ce:surname>Taylor</ce:surname><ce:given-name>D.P.</ce:given-name></sb:author></sb:authors></sb:contribution><sb:host><sb:issue><sb:series><sb:title><sb:maintitle>Trends Pharmacol. Sci.</sb:maintitle></sb:title><sb:volume-nr>13</sb:volume-nr></sb:series><sb:date>1992</sb:date></sb:issue><sb:pages><sb:first-page>85</sb:first-page><sb:last-page>86</sb:last-page></sb:pages></sb:host></sb:reference></ce:bib-reference><ce:bib-reference id="bib5"><ce:label>[5]</ce:label><sb:reference><sb:contribution langtype="en"><sb:authors><sb:author><ce:surname>Musacchio</ce:surname><ce:given-name>J.M.</ce:given-name></sb:author><sb:author><ce:surname>Klein</ce:surname><ce:given-name>M.</ce:given-name></sb:author><sb:author><ce:surname>Paturzo</ce:surname><ce:given-name>J.</ce:given-name></sb:author></sb:authors></sb:contribution><sb:host><sb:issue><sb:series><sb:title><sb:maintitle>J. Mol. Pharmacol.</sb:maintitle></sb:title><sb:volume-nr>35</sb:volume-nr></sb:series><sb:date>1989</sb:date></sb:issue><sb:pages><sb:first-page>1</sb:first-page><sb:last-page>5</sb:last-page></sb:pages></sb:host></sb:reference></ce:bib-reference><ce:bib-reference id="bib6"><ce:label>[6]</ce:label><sb:reference><sb:contribution langtype="en"><sb:authors><sb:author><ce:surname>Zhou</ce:surname><ce:given-name>G.Z.</ce:given-name></sb:author><sb:author><ce:surname>Musacchio</ce:surname><ce:given-name>J.M.</ce:given-name></sb:author></sb:authors></sb:contribution><sb:host><sb:issue><sb:series><sb:title><sb:maintitle>Eur. J. Pharmacol.</sb:maintitle></sb:title><sb:volume-nr>206</sb:volume-nr></sb:series><sb:date>1991</sb:date></sb:issue><sb:pages><sb:first-page>261</sb:first-page><sb:last-page>269</sb:last-page></sb:pages></sb:host></sb:reference></ce:bib-reference><ce:bib-reference id="bib7"><ce:label>Hellewell and Bowen, 1990</ce:label><sb:reference><sb:contribution langtype="en"><sb:authors><sb:author><ce:surname>Hellewell</ce:surname><ce:given-name>S.B.</ce:given-name></sb:author><sb:author><ce:surname>Bowen</ce:surname><ce:given-name>W.D.</ce:given-name></sb:author></sb:authors></sb:contribution><sb:host><sb:issue><sb:series><sb:title><sb:maintitle>Brain Res.</sb:maintitle></sb:title><sb:volume-nr>527</sb:volume-nr></sb:series><sb:date>1990</sb:date></sb:issue><sb:pages><sb:first-page>244</sb:first-page><sb:last-page>253</sb:last-page></sb:pages></sb:host></sb:reference></ce:bib-reference><ce:bib-reference id="bib8"><ce:label>[7]</ce:label><sb:reference><sb:contribution langtype="en"><sb:authors><sb:author><ce:surname>Walker</ce:surname><ce:given-name>J.M.</ce:given-name></sb:author><sb:author><ce:surname>Bowen</ce:surname><ce:given-name>W.D.</ce:given-name></sb:author><sb:author><ce:surname>Goldstein</ce:surname><ce:given-name>S.R.</ce:given-name></sb:author><sb:author><ce:surname>Roberts</ce:surname><ce:given-name>A.H.</ce:given-name></sb:author><sb:author><ce:surname>Patrick</ce:surname><ce:given-name>S.L.</ce:given-name></sb:author><sb:author><ce:surname>Hohmann</ce:surname><ce:given-name>A.G.</ce:given-name></sb:author></sb:authors></sb:contribution><sb:host><sb:issue><sb:series><sb:title><sb:maintitle>Brain Res.</sb:maintitle></sb:title><sb:volume-nr>581</sb:volume-nr></sb:series><sb:date>1992</sb:date></sb:issue><sb:pages><sb:first-page>33</sb:first-page><sb:last-page>38</sb:last-page></sb:pages></sb:host></sb:reference></ce:bib-reference><ce:bib-reference id="bib9"><ce:label>[8]</ce:label><sb:reference><sb:contribution langtype="en"><sb:authors><sb:author><ce:surname>Myers</ce:surname><ce:given-name>A.M.</ce:given-name></sb:author><sb:author><ce:surname>Charifson</ce:surname><ce:given-name>P.S.</ce:given-name></sb:author><sb:author><ce:surname>Owens</ce:surname><ce:given-name>C.E.</ce:given-name></sb:author><sb:author><ce:surname>Kula</ce:surname><ce:given-name>N.S.</ce:given-name></sb:author><sb:author><ce:surname>Mc Phail</ce:surname><ce:given-name>A.T.</ce:given-name></sb:author><sb:author><ce:surname>Baldessarini</ce:surname><ce:given-name>R.J.</ce:given-name></sb:author><sb:author><ce:surname>Booth</ce:surname><ce:given-name>R.G.</ce:given-name></sb:author><sb:author><ce:surname>Dwyrick</ce:surname><ce:given-name>S.</ce:given-name></sb:author></sb:authors></sb:contribution><sb:host><sb:issue><sb:series><sb:title><sb:maintitle>J. Med. Chem.</sb:maintitle></sb:title><sb:volume-nr>37</sb:volume-nr></sb:series><sb:date>1994</sb:date></sb:issue><sb:pages><sb:first-page>4109</sb:first-page><sb:last-page>4217</sb:last-page></sb:pages></sb:host></sb:reference></ce:bib-reference><ce:bib-reference id="bib10"><ce:label>[9]</ce:label><sb:reference><sb:contribution langtype="en"><sb:authors><sb:author><ce:surname>Schwarcz</ce:surname><ce:given-name>G.</ce:given-name></sb:author><sb:author><ce:surname>Halaris</ce:surname><ce:given-name>A.</ce:given-name></sb:author><sb:author><ce:surname>Dren</ce:surname><ce:given-name>A.</ce:given-name></sb:author><sb:author><ce:surname>Manberg</ce:surname><ce:given-name>P.</ce:given-name></sb:author></sb:authors></sb:contribution><sb:host><sb:issue><sb:series><sb:title><sb:maintitle>Drug Dev. Res.</sb:maintitle></sb:title><sb:volume-nr>5</sb:volume-nr></sb:series><sb:date>1985</sb:date></sb:issue><sb:pages><sb:first-page>387</sb:first-page><sb:last-page>393</sb:last-page></sb:pages></sb:host></sb:reference></ce:bib-reference><ce:bib-reference id="bib11"><ce:label>[10]</ce:label><sb:reference><sb:contribution langtype="en"><sb:authors><sb:author><ce:surname>Erickson</ce:surname><ce:given-name>R.H.</ce:given-name></sb:author><sb:author><ce:surname>Natalie</ce:surname><ce:given-name>K.J.</ce:given-name></sb:author><sb:author><ce:surname>Bock</ce:surname><ce:given-name>W.</ce:given-name></sb:author><sb:author><ce:surname>Lu</ce:surname><ce:given-name>Z.</ce:given-name></sb:author><sb:author><ce:surname>Farzin</ce:surname><ce:given-name>F.</ce:given-name></sb:author><sb:author><ce:surname>Sherrill</ce:surname><ce:given-name>R.G.</ce:given-name></sb:author><sb:author><ce:surname>Meloni</ce:surname><ce:given-name>D.J.</ce:given-name></sb:author><sb:author><ce:surname>Patch</ce:surname><ce:given-name>R.J.</ce:given-name></sb:author><sb:author><ce:surname>Rzesotarski</ce:surname><ce:given-name>W.J.</ce:given-name></sb:author><sb:author><ce:surname>Clifton</ce:surname><ce:given-name>J.</ce:given-name></sb:author><sb:author><ce:surname>Pontecorvo</ce:surname><ce:given-name>M.J.</ce:given-name></sb:author><sb:author><ce:surname>Bailey</ce:surname><ce:given-name>M.A.</ce:given-name></sb:author><sb:author><ce:surname>Naper</ce:surname><ce:given-name>K.</ce:given-name></sb:author><sb:author><ce:surname>Karbon</ce:surname><ce:given-name>W</ce:given-name></sb:author></sb:authors></sb:contribution><sb:host><sb:issue><sb:series><sb:title><sb:maintitle>J. Med. Chem.</sb:maintitle></sb:title><sb:volume-nr>35</sb:volume-nr></sb:series><sb:date>1992</sb:date></sb:issue><sb:pages><sb:first-page>1526</sb:first-page><sb:last-page>1535</sb:last-page></sb:pages></sb:host></sb:reference></ce:bib-reference><ce:bib-reference id="bib12"><ce:label>[11]</ce:label><sb:reference><sb:contribution langtype="en"><sb:authors><sb:author><ce:surname>Erikson</ce:surname><ce:given-name>J.</ce:given-name></sb:author><sb:author><ce:surname>Natalie</ce:surname><ce:given-name>K.J.</ce:given-name></sb:author><sb:author><ce:surname>Bock</ce:surname><ce:given-name>W.</ce:given-name></sb:author><sb:author><ce:surname>Lu</ce:surname><ce:given-name>Z.</ce:given-name></sb:author><sb:author><ce:surname>Farzin</ce:surname><ce:given-name>F.</ce:given-name></sb:author><sb:author><ce:surname>Sherrill</ce:surname><ce:given-name>R.G.</ce:given-name></sb:author><sb:author><ce:surname>Melani</ce:surname><ce:given-name>D.J.</ce:given-name></sb:author><sb:author><ce:surname>Patch</ce:surname><ce:given-name>R.J.</ce:given-name></sb:author><sb:author><ce:surname>Rzesotarski</ce:surname><ce:given-name>W.J.</ce:given-name></sb:author><sb:author><ce:surname>Clifton</ce:surname><ce:given-name>J.</ce:given-name></sb:author><sb:author><ce:surname>Pontecorro</ce:surname><ce:given-name>M.J.</ce:given-name></sb:author><sb:author><ce:surname>Bailey</ce:surname><ce:given-name>M.M.</ce:given-name></sb:author><sb:author><ce:surname>Noyer</ce:surname><ce:given-name>K.</ce:given-name></sb:author><sb:author><ce:surname>Karbon</ce:surname><ce:given-name>W.</ce:given-name></sb:author></sb:authors></sb:contribution><sb:host><sb:issue><sb:series><sb:title><sb:maintitle>J. Med. Chem.</sb:maintitle></sb:title><sb:volume-nr>35</sb:volume-nr></sb:series><sb:date>1992</sb:date></sb:issue><sb:pages><sb:first-page>1526</sb:first-page><sb:last-page>1535</sb:last-page></sb:pages></sb:host></sb:reference></ce:bib-reference><ce:bib-reference id="bib13"><ce:label>[12]</ce:label><sb:reference><sb:contribution langtype="en"><sb:authors><sb:author><ce:surname>McLean</ce:surname><ce:given-name>S.</ce:given-name></sb:author><sb:author><ce:surname>Weber</ce:surname><ce:given-name>E.</ce:given-name></sb:author></sb:authors></sb:contribution><sb:host><sb:issue><sb:series><sb:title><sb:maintitle>Neuroscience</sb:maintitle></sb:title><sb:volume-nr>25</sb:volume-nr></sb:series><sb:date>1988</sb:date></sb:issue><sb:pages><sb:first-page>259</sb:first-page><sb:last-page>269</sb:last-page></sb:pages></sb:host></sb:reference></ce:bib-reference><ce:bib-reference id="bib14"><ce:label>[13]</ce:label><sb:reference><sb:contribution langtype="en"><sb:authors><sb:author><ce:surname>Matsumoto</ce:surname><ce:given-name>R.R.</ce:given-name></sb:author><sb:author><ce:surname>Hemstreet</ce:surname><ce:given-name>M.K.</ce:given-name></sb:author><sb:author><ce:surname>Lai</ce:surname><ce:given-name>N.L.</ce:given-name></sb:author><sb:author><ce:surname>Thurkauf</ce:surname><ce:given-name>A.</ce:given-name></sb:author><sb:author><ce:surname>De Costa</ce:surname><ce:given-name>B.R.</ce:given-name></sb:author><sb:author><ce:surname>Rice</ce:surname><ce:given-name>K.C.</ce:given-name></sb:author><sb:author><ce:surname>Hellewell</ce:surname><ce:given-name>S.B.</ce:given-name></sb:author><sb:author><ce:surname>Bowen</ce:surname><ce:given-name>W.D.</ce:given-name></sb:author><sb:author><ce:surname>Walker</ce:surname><ce:given-name>J.M.</ce:given-name></sb:author></sb:authors></sb:contribution><sb:host><sb:issue><sb:series><sb:title><sb:maintitle>Pharmacol. Biochem. Behav.</sb:maintitle></sb:title><sb:volume-nr>36</sb:volume-nr></sb:series><sb:date>1990</sb:date></sb:issue><sb:pages><sb:first-page>151</sb:first-page><sb:last-page>155</sb:last-page></sb:pages></sb:host></sb:reference></ce:bib-reference><ce:bib-reference id="bib15"><ce:label>[14]</ce:label><sb:reference><sb:contribution langtype="en"><sb:authors><sb:author><ce:surname>Wolfe</ce:surname><ce:given-name>S.A.</ce:given-name><ce:suffix>Jr.</ce:suffix></sb:author><sb:author><ce:surname>Culp</ce:surname><ce:given-name>S.G.</ce:given-name></sb:author><sb:author><ce:surname>De Souza</ce:surname><ce:given-name>E.B.</ce:given-name></sb:author></sb:authors></sb:contribution><sb:host><sb:issue><sb:series><sb:title><sb:maintitle>Endocrinology</sb:maintitle></sb:title><sb:volume-nr>124</sb:volume-nr></sb:series><sb:date>1989</sb:date></sb:issue><sb:pages><sb:first-page>1160</sb:first-page><sb:last-page>1172</sb:last-page></sb:pages></sb:host></sb:reference></ce:bib-reference><ce:bib-reference id="bib16"><ce:label>[15]</ce:label><sb:reference><sb:contribution langtype="en"><sb:authors><sb:author><ce:surname>Su</ce:surname><ce:given-name>T.P.</ce:given-name></sb:author><sb:author><ce:surname>Schell</ce:surname><ce:given-name>S.E.</ce:given-name></sb:author><sb:author><ce:surname>Ford-Rice</ce:surname><ce:given-name>F.Y.</ce:given-name></sb:author><sb:author><ce:surname>London</ce:surname><ce:given-name>E.D.</ce:given-name></sb:author></sb:authors></sb:contribution><sb:host><sb:issue><sb:series><sb:title><sb:maintitle>Eur. J. Pharmacol.</sb:maintitle></sb:title><sb:volume-nr>148</sb:volume-nr></sb:series><sb:date>1988</sb:date></sb:issue><sb:pages><sb:first-page>467</sb:first-page><sb:last-page>470</sb:last-page></sb:pages></sb:host></sb:reference></ce:bib-reference><ce:bib-reference id="bib17"><ce:label>[16]</ce:label><sb:reference><sb:contribution langtype="en"><sb:authors><sb:author><ce:surname>Wolfe</ce:surname><ce:given-name>S.A.</ce:given-name><ce:suffix>Jr.</ce:suffix></sb:author><sb:author><ce:surname>Kulsakdnun</ce:surname><ce:given-name>C.</ce:given-name></sb:author><sb:author><ce:surname>Battaglia</ce:surname><ce:given-name>G.</ce:given-name></sb:author><sb:author><ce:surname>Jaffre</ce:surname><ce:given-name>J.H.</ce:given-name></sb:author><sb:author><ce:surname>De Souza</ce:surname><ce:given-name>E.B.</ce:given-name></sb:author></sb:authors></sb:contribution><sb:host><sb:issue><sb:series><sb:title><sb:maintitle>J. Pharmacol. Exp. Ther.</sb:maintitle></sb:title><sb:volume-nr>247</sb:volume-nr></sb:series><sb:date>1988</sb:date></sb:issue><sb:pages><sb:first-page>1114</sb:first-page><sb:last-page>1119</sb:last-page></sb:pages></sb:host></sb:reference></ce:bib-reference><ce:bib-reference id="bib18"><ce:label>[17]</ce:label><sb:reference><sb:contribution langtype="en"><sb:authors><sb:author><ce:surname>Massamiri</ce:surname><ce:given-name>T.</ce:given-name></sb:author><sb:author><ce:surname>Duckles</ce:surname><ce:given-name>S.P.</ce:given-name></sb:author></sb:authors></sb:contribution><sb:host><sb:issue><sb:series><sb:title><sb:maintitle>J. Pharmacol. Exp. Ther.</sb:maintitle></sb:title><sb:volume-nr>253</sb:volume-nr></sb:series><sb:date>1990</sb:date></sb:issue><sb:pages><sb:first-page>124</sb:first-page><sb:last-page>129</sb:last-page></sb:pages></sb:host></sb:reference></ce:bib-reference><ce:bib-reference id="bib19"><ce:label>[18]</ce:label><sb:reference><sb:contribution langtype="en"><sb:authors><sb:author><ce:surname>Massamiri</ce:surname><ce:given-name>T.</ce:given-name></sb:author><sb:author><ce:surname>Duckles</ce:surname><ce:given-name>S.P.</ce:given-name></sb:author></sb:authors></sb:contribution><sb:host><sb:issue><sb:series><sb:title><sb:maintitle>J. Pharmacol. Exp. Ther.</sb:maintitle></sb:title><sb:volume-nr>256</sb:volume-nr></sb:series><sb:date>1991</sb:date></sb:issue><sb:pages><sb:first-page>519</sb:first-page><sb:last-page>524</sb:last-page></sb:pages></sb:host></sb:reference></ce:bib-reference><ce:bib-reference id="bib20"><ce:label>[19]</ce:label><sb:reference><sb:contribution langtype="en"><sb:authors><sb:author><ce:surname>Su</ce:surname><ce:given-name>T.P.</ce:given-name></sb:author><sb:author><ce:surname>London</ce:surname><ce:given-name>E.D.</ce:given-name></sb:author><sb:author><ce:surname>Jaffe</ce:surname><ce:given-name>J.H.</ce:given-name></sb:author></sb:authors></sb:contribution><sb:host><sb:issue><sb:series><sb:title><sb:maintitle>Science</sb:maintitle></sb:title><sb:volume-nr>240</sb:volume-nr></sb:series><sb:date>1988</sb:date></sb:issue><sb:pages><sb:first-page>219</sb:first-page><sb:last-page>221</sb:last-page></sb:pages></sb:host></sb:reference></ce:bib-reference><ce:bib-reference id="bib21"><ce:label>[20]</ce:label><sb:reference><sb:contribution langtype="en"><sb:authors><sb:author><ce:surname>Snyder</ce:surname><ce:given-name>S.H.</ce:given-name></sb:author><sb:author><ce:surname>Largent</ce:surname><ce:given-name>B.L.</ce:given-name></sb:author></sb:authors></sb:contribution><sb:host><sb:issue><sb:series><sb:title><sb:maintitle>J. Neuropsychiatry</sb:maintitle></sb:title><sb:volume-nr>1</sb:volume-nr></sb:series><sb:date>1989</sb:date></sb:issue><sb:pages><sb:first-page>7</sb:first-page><sb:last-page>15</sb:last-page></sb:pages></sb:host></sb:reference></ce:bib-reference><ce:bib-reference id="bib22"><ce:label>[21]</ce:label><sb:reference><sb:contribution langtype="en"><sb:authors><sb:author><ce:surname>Abou-Gharbia</ce:surname><ce:given-name>M.</ce:given-name></sb:author><sb:author><ce:surname>Ablordeppey</ce:surname><ce:given-name>S.Y.</ce:given-name></sb:author><sb:author><ce:surname>Glennon</ce:surname><ce:given-name>R.A.</ce:given-name></sb:author></sb:authors></sb:contribution><sb:host><sb:issue><sb:series><sb:title><sb:maintitle>Ann. Rep. Med. Chem.</sb:maintitle></sb:title><sb:volume-nr>28</sb:volume-nr></sb:series><sb:date>1993</sb:date></sb:issue><sb:pages><sb:first-page>1</sb:first-page><sb:last-page>10</sb:last-page></sb:pages></sb:host></sb:reference></ce:bib-reference><ce:bib-reference id="bib23"><ce:label>[22]</ce:label><sb:reference><sb:contribution langtype="en"><sb:authors><sb:author><ce:surname>Contreras</ce:surname><ce:given-name>P.C.</ce:given-name></sb:author><sb:author><ce:surname>Ragan</ce:surname><ce:given-name>D.M.</ce:given-name></sb:author><sb:author><ce:surname>Bremer</ce:surname><ce:given-name>M.E.</ce:given-name></sb:author><sb:author><ce:surname>Lanthom</ce:surname><ce:given-name>T.H.</ce:given-name></sb:author><sb:author><ce:surname>Grazy</ce:surname><ce:given-name>N.M.</ce:given-name></sb:author><sb:author><ce:surname>Iyengar</ce:surname><ce:given-name>S.</ce:given-name></sb:author><sb:author><ce:surname>Jacobson</ce:surname><ce:given-name>A.E.</ce:given-name></sb:author><sb:author><ce:surname>Rice</ce:surname><ce:given-name>K.C.</ce:given-name></sb:author><sb:author><ce:surname>De Costa</ce:surname><ce:given-name>B.R.</ce:given-name></sb:author></sb:authors></sb:contribution><sb:host><sb:issue><sb:series><sb:title><sb:maintitle>Brain Res.</sb:maintitle></sb:title><sb:volume-nr>546</sb:volume-nr></sb:series><sb:date>1991</sb:date></sb:issue><sb:pages><sb:first-page>79</sb:first-page><sb:last-page>82</sb:last-page></sb:pages></sb:host></sb:reference></ce:bib-reference><ce:bib-reference id="bib24"><ce:label>[23]</ce:label><sb:reference><sb:contribution langtype="en"><sb:authors><sb:author><ce:surname>Contreras</ce:surname><ce:given-name>P.C.</ce:given-name></sb:author><sb:author><ce:surname>Gray</ce:surname><ce:given-name>N.</ce:given-name></sb:author><sb:author><ce:surname>Ragan</ce:surname><ce:given-name>D.</ce:given-name></sb:author><sb:author><ce:surname>Lathorn</ce:surname><ce:given-name>B.E.</ce:given-name></sb:author></sb:authors></sb:contribution><sb:host><sb:issue><sb:series><sb:title><sb:maintitle>Life Sci.</sb:maintitle></sb:title><sb:volume-nr>51</sb:volume-nr></sb:series><sb:date>1992</sb:date></sb:issue><sb:pages><sb:first-page>1145</sb:first-page><sb:last-page>1149</sb:last-page></sb:pages></sb:host></sb:reference></ce:bib-reference><ce:bib-reference id="bib25"><ce:label>[24]</ce:label><sb:reference><sb:contribution langtype="en"><sb:authors><sb:author><ce:surname>Earley</ce:surname><ce:given-name>B.</ce:given-name></sb:author><sb:author><ce:surname>Burke</ce:surname><ce:given-name>M.</ce:given-name></sb:author><sb:author><ce:surname>Leonard</ce:surname><ce:given-name>B.E.</ce:given-name></sb:author><sb:author><ce:surname>Gournet</ce:surname><ce:given-name>G.J.</ce:given-name></sb:author><sb:author><ce:surname>Junien</ce:surname><ce:given-name>J.L.</ce:given-name></sb:author></sb:authors></sb:contribution><sb:host><sb:issue><sb:series><sb:title><sb:maintitle>Brain Res.</sb:maintitle></sb:title><sb:volume-nr>546</sb:volume-nr></sb:series><sb:date>1991</sb:date></sb:issue><sb:pages><sb:first-page>282</sb:first-page><sb:last-page>286</sb:last-page></sb:pages></sb:host></sb:reference></ce:bib-reference><ce:bib-reference id="bib26"><ce:label>[25]</ce:label><sb:reference><sb:contribution langtype="en"><sb:authors><sb:author><ce:surname>Kauser</ce:surname><ce:given-name>C.</ce:given-name></sb:author><sb:author><ce:surname>Pontecorvo</ce:surname><ce:given-name>R.J.</ce:given-name></sb:author><sb:author><ce:surname>Meshaw</ce:surname><ce:given-name>R.E.</ce:given-name></sb:author></sb:authors></sb:contribution><sb:host><sb:issue><sb:series><sb:title><sb:maintitle>Neurotransmissions</sb:maintitle></sb:title><sb:volume-nr>7</sb:volume-nr></sb:series><sb:date>1991</sb:date></sb:issue><sb:pages><sb:first-page>1</sb:first-page><sb:last-page>5</sb:last-page></sb:pages></sb:host></sb:reference></ce:bib-reference><ce:bib-reference id="bib27"><ce:label>[26]</ce:label><sb:reference><sb:contribution langtype="en"><sb:authors><sb:author><ce:surname>Derocq</ce:surname><ce:given-name>J.M.</ce:given-name></sb:author><sb:author><ce:surname>Bourrie</ce:surname><ce:given-name>B.</ce:given-name></sb:author><sb:author><ce:surname>Segui</ce:surname><ce:given-name>M.</ce:given-name></sb:author><sb:author><ce:surname>Lefur</ce:surname><ce:given-name>G.</ce:given-name></sb:author><sb:author><ce:surname>Casellas</ce:surname><ce:given-name>P.</ce:given-name></sb:author></sb:authors></sb:contribution><sb:host><sb:issue><sb:series><sb:title><sb:maintitle>J. Pharmacol Exp. Ther.</sb:maintitle></sb:title><sb:volume-nr>272</sb:volume-nr></sb:series><sb:date>1995</sb:date></sb:issue><sb:pages><sb:first-page>224</sb:first-page><sb:last-page>230</sb:last-page></sb:pages></sb:host></sb:reference></ce:bib-reference><ce:bib-reference id="bib28"><ce:label>[27]</ce:label><sb:reference><sb:contribution langtype="en"><sb:authors><sb:author><ce:surname>Baziard-Mouysset</ce:surname><ce:given-name>G.</ce:given-name></sb:author><sb:author><ce:surname>De Saqui-Sannes</ce:surname><ce:given-name>G.P.</ce:given-name></sb:author><sb:author><ce:surname>Younes</ce:surname><ce:given-name>S.</ce:given-name></sb:author><sb:author><ce:surname>Labssita</ce:surname><ce:given-name>Y.</ce:given-name></sb:author><sb:author><ce:surname>Payard</ce:surname><ce:given-name>M.</ce:given-name></sb:author><sb:author><ce:surname>Caignard</ce:surname><ce:given-name>D.H.</ce:given-name></sb:author><sb:author><ce:surname>Rettori</ce:surname><ce:given-name>M.C.</ce:given-name></sb:author><sb:author><ce:surname>Guardiola-Lemaitre</ce:surname><ce:given-name>B.</ce:given-name></sb:author><sb:author><ce:surname>Renard</ce:surname><ce:given-name>P.</ce:given-name></sb:author></sb:authors></sb:contribution><sb:host><sb:issue><sb:series><sb:title><sb:maintitle>J. Pharm. Belg.</sb:maintitle></sb:title><sb:volume-nr>2</sb:volume-nr></sb:series><sb:date>1995</sb:date></sb:issue><sb:pages><sb:first-page>162</sb:first-page><sb:last-page>166</sb:last-page></sb:pages></sb:host></sb:reference></ce:bib-reference><ce:bib-reference id="bib29"><ce:label>[28]</ce:label><sb:reference><sb:contribution langtype="en"><sb:authors><sb:author><ce:surname>Sami</ce:surname><ce:given-name>S.M.</ce:given-name></sb:author><sb:author><ce:surname>Ibrahim</ce:surname><ce:given-name>S.S.</ce:given-name></sb:author><sb:author><ce:surname>Abdel-Halim</ce:surname><ce:given-name>A.M.</ce:given-name></sb:author><sb:author><ce:surname>Aly</ce:surname><ce:given-name>Y.L.</ce:given-name></sb:author></sb:authors></sb:contribution><sb:host><sb:issue><sb:series><sb:title><sb:maintitle>Ind. J. Chem. Sect. B.</sb:maintitle></sb:title><sb:volume-nr>25 B</sb:volume-nr></sb:series><sb:issue-nr>4</sb:issue-nr><sb:date>1986</sb:date></sb:issue><sb:pages><sb:first-page>384</sb:first-page><sb:last-page>389</sb:last-page></sb:pages></sb:host></sb:reference></ce:bib-reference><ce:bib-reference id="bib30"><ce:label>[29]</ce:label><sb:reference><sb:contribution langtype="en"><sb:authors><sb:author><ce:surname>Hsu</ce:surname><ce:given-name>K.K.</ce:given-name></sb:author><sb:author><ce:surname>Lin</ce:surname><ce:given-name>Y.C.</ce:given-name></sb:author><sb:author><ce:surname>Su</ce:surname><ce:given-name>C.T.</ce:given-name></sb:author><sb:author><ce:surname>Lien</ce:surname><ce:given-name>E.J.</ce:given-name></sb:author></sb:authors></sb:contribution><sb:host><sb:issue><sb:series><sb:title><sb:maintitle>Taiwan Yao H. Tsa Chich.</sb:maintitle></sb:title><sb:volume-nr>34</sb:volume-nr></sb:series><sb:issue-nr>2</sb:issue-nr><sb:date>1982</sb:date></sb:issue><sb:pages><sb:first-page>71</sb:first-page><sb:last-page>86</sb:last-page></sb:pages></sb:host></sb:reference></ce:bib-reference><ce:bib-reference id="bib31"><ce:label>[30]</ce:label><sb:reference><sb:contribution langtype="en"><sb:authors><sb:author><ce:surname>Ellis</ce:surname><ce:given-name>G.P.</ce:given-name></sb:author><sb:author><ce:surname>Shaw</ce:surname><ce:given-name>D.</ce:given-name></sb:author></sb:authors></sb:contribution><sb:host><sb:issue><sb:series><sb:title><sb:maintitle>J. Med. Chem.</sb:maintitle></sb:title><sb:volume-nr>15</sb:volume-nr></sb:series><sb:issue-nr>8</sb:issue-nr><sb:date>1972</sb:date></sb:issue><sb:pages><sb:first-page>865</sb:first-page><sb:last-page>867</sb:last-page></sb:pages></sb:host></sb:reference></ce:bib-reference><ce:bib-reference id="bib32"><ce:label>[31]</ce:label><sb:reference><sb:comment>2307828</sb:comment><sb:contribution langtype="en"><sb:authors><sb:author><ce:surname>Dorn</ce:surname><ce:given-name>C.P.</ce:given-name><ce:suffix>Jr.</ce:suffix></sb:author><sb:author><ce:surname>Brevet</ce:surname><ce:given-name>DE</ce:given-name></sb:author></sb:authors></sb:contribution><sb:host><sb:issue><sb:series><sb:title><sb:maintitle>Chem. Abstr. 79</sb:maintitle></sb:title><sb:volume-nr>137</sb:volume-nr></sb:series><sb:date>1973</sb:date></sb:issue><sb:pages><sb:first-page>137</sb:first-page></sb:pages></sb:host></sb:reference><sb:reference><sb:comment>2307828</sb:comment><sb:contribution langtype="en"><sb:authors><sb:author><ce:surname>Dorn</ce:surname><ce:given-name>C.P.</ce:given-name><ce:suffix>Jr.</ce:suffix></sb:author><sb:author><ce:surname>Brevet</ce:surname><ce:given-name>DE</ce:given-name></sb:author></sb:authors></sb:contribution><sb:host><sb:issue><sb:series><sb:title><sb:maintitle>Chem. Abstr. 79</sb:maintitle></sb:title><sb:volume-nr>137</sb:volume-nr></sb:series><sb:date>1973</sb:date></sb:issue><sb:pages><sb:first-page>1310</sb:first-page></sb:pages></sb:host></sb:reference></ce:bib-reference><ce:bib-reference id="bib33"><ce:label>[32]</ce:label><sb:reference><sb:contribution langtype="en"><sb:authors><sb:author><ce:surname>De Costa</ce:surname><ce:given-name>B.R.</ce:given-name></sb:author><sb:author><ce:surname>Rice</ce:surname><ce:given-name>K.C.</ce:given-name></sb:author><sb:author><ce:surname>Bowen</ce:surname><ce:given-name>W.D.</ce:given-name></sb:author><sb:author><ce:surname>Thurkauf</ce:surname><ce:given-name>A.</ce:given-name></sb:author><sb:author><ce:surname>Rothman</ce:surname><ce:given-name>R.B.</ce:given-name></sb:author><sb:author><ce:surname>Jacobson</ce:surname><ce:given-name>A.E.</ce:given-name></sb:author><sb:author><ce:surname>Radesca</ce:surname><ce:given-name>L.</ce:given-name></sb:author><sb:author><ce:surname>Contreras</ce:surname><ce:given-name>P.C.</ce:given-name></sb:author><sb:author><ce:surname>Grayn</ce:surname><ce:given-name>M.</ce:given-name></sb:author><sb:author><ce:surname>Daly</ce:surname><ce:given-name>I.</ce:given-name></sb:author><sb:author><ce:surname>Iyengar</ce:surname><ce:given-name>S.</ce:given-name></sb:author><sb:author><ce:surname>Walker</ce:surname><ce:given-name>J.M.</ce:given-name></sb:author></sb:authors></sb:contribution><sb:host><sb:issue><sb:series><sb:title><sb:maintitle>J. Med. Chem.</sb:maintitle></sb:title><sb:volume-nr>33</sb:volume-nr></sb:series><sb:date>1990</sb:date></sb:issue><sb:pages><sb:first-page>3100</sb:first-page><sb:last-page>3110</sb:last-page></sb:pages></sb:host></sb:reference></ce:bib-reference><ce:bib-reference id="bib34"><ce:label>[33]</ce:label><sb:reference><sb:contribution langtype="en"><sb:authors><sb:author><ce:surname>Payard</ce:surname><ce:given-name>M.</ce:given-name></sb:author></sb:authors></sb:contribution><sb:host><sb:issue><sb:series><sb:title><sb:maintitle>Bull. Soc. Chim. Fr.</sb:maintitle></sb:title><sb:volume-nr>7–8</sb:volume-nr></sb:series><sb:date>1973</sb:date></sb:issue><sb:pages><sb:first-page>2392</sb:first-page></sb:pages></sb:host></sb:reference></ce:bib-reference><ce:bib-reference id="bib35"><ce:label>[34]</ce:label><sb:reference><sb:contribution langtype="en"><sb:authors><sb:author><ce:surname>Mouysset</ce:surname><ce:given-name>G.</ce:given-name></sb:author><sb:author><ce:surname>Payard</ce:surname><ce:given-name>M.</ce:given-name></sb:author><sb:author><ce:surname>Tronche</ce:surname><ce:given-name>P.</ce:given-name></sb:author><sb:author><ce:surname>Bastide</ce:surname><ce:given-name>J.</ce:given-name></sb:author><sb:author><ce:surname>Bastide</ce:surname><ce:given-name>P.</ce:given-name></sb:author></sb:authors></sb:contribution><sb:host><sb:issue><sb:series><sb:title><sb:maintitle>Eur. J. Med. Chem.</sb:maintitle></sb:title><sb:volume-nr>23</sb:volume-nr></sb:series><sb:date>1988</sb:date></sb:issue><sb:pages><sb:first-page>199</sb:first-page><sb:last-page>202</sb:last-page></sb:pages></sb:host></sb:reference></ce:bib-reference><ce:bib-reference id="bib36"><ce:label>[35]</ce:label><sb:reference><sb:contribution langtype="en"><sb:authors><sb:author><ce:surname>Payard</ce:surname><ce:given-name>M.</ce:given-name></sb:author><sb:author><ce:surname>Mouysset</ce:surname><ce:given-name>G.</ce:given-name></sb:author><sb:author><ce:surname>Tronche</ce:surname><ce:given-name>P.</ce:given-name></sb:author><sb:author><ce:surname>Bastide</ce:surname><ce:given-name>P.</ce:given-name></sb:author><sb:author><ce:surname>Bastide</ce:surname><ce:given-name>J.</ce:given-name></sb:author></sb:authors></sb:contribution><sb:host><sb:issue><sb:series><sb:title><sb:maintitle>Eur. J. Med. Chem.</sb:maintitle></sb:title><sb:volume-nr>20</sb:volume-nr></sb:series><sb:date>1985</sb:date></sb:issue><sb:pages><sb:first-page>117</sb:first-page><sb:last-page>120</sb:last-page></sb:pages></sb:host></sb:reference></ce:bib-reference><ce:bib-reference id="bib37"><ce:label>[36]</ce:label><sb:reference><sb:contribution langtype="en"><sb:authors><sb:author><ce:surname>Mouysset</ce:surname><ce:given-name>G.</ce:given-name></sb:author><sb:author><ce:surname>Payard</ce:surname><ce:given-name>M.</ce:given-name></sb:author><sb:author><ce:surname>Grassy</ce:surname><ce:given-name>G.</ce:given-name></sb:author><sb:author><ce:surname>Tronche</ce:surname><ce:given-name>P.</ce:given-name></sb:author><sb:author><ce:surname>Dabire</ce:surname><ce:given-name>H.</ce:given-name></sb:author><sb:author><ce:surname>Mouille</ce:surname><ce:given-name>P.</ce:given-name></sb:author><sb:author><ce:surname>Schmitt</ce:surname><ce:given-name>H.</ce:given-name></sb:author></sb:authors></sb:contribution><sb:host><sb:issue><sb:series><sb:title><sb:maintitle>Eur. J. Med. Chem.</sb:maintitle></sb:title><sb:volume-nr>22</sb:volume-nr></sb:series><sb:date>1987</sb:date></sb:issue><sb:pages><sb:first-page>539</sb:first-page><sb:last-page>544</sb:last-page></sb:pages></sb:host></sb:reference></ce:bib-reference><ce:bib-reference id="bib38"><ce:label>[37]</ce:label><sb:reference><sb:contribution langtype="en"><sb:authors><sb:author><ce:surname>Karbon</ce:surname><ce:given-name>E.W.</ce:given-name></sb:author><sb:author><ce:surname>Naper</ce:surname><ce:given-name>K.</ce:given-name></sb:author><sb:author><ce:surname>Pontecorvo</ce:surname><ce:given-name>M.J.</ce:given-name></sb:author></sb:authors></sb:contribution><sb:host><sb:issue><sb:series><sb:title><sb:maintitle>Eur. J. Pharmacol.</sb:maintitle></sb:title><sb:volume-nr>193</sb:volume-nr></sb:series><sb:date>1991</sb:date></sb:issue><sb:pages><sb:first-page>21</sb:first-page><sb:last-page>27</sb:last-page></sb:pages></sb:host></sb:reference></ce:bib-reference><ce:bib-reference id="bib39"><ce:label>[38]</ce:label><sb:reference><sb:contribution langtype="en"><sb:authors><sb:author><ce:surname>Hoyer</ce:surname><ce:given-name>D.</ce:given-name></sb:author><sb:author><ce:surname>Engel</ce:surname><ce:given-name>G.</ce:given-name></sb:author><sb:author><ce:surname>Kalkman</ce:surname><ce:given-name>H.O.</ce:given-name></sb:author></sb:authors></sb:contribution><sb:host><sb:issue><sb:series><sb:title><sb:maintitle>Eur. J. Pharmacol.</sb:maintitle></sb:title><sb:volume-nr>118</sb:volume-nr></sb:series><sb:date>1985</sb:date></sb:issue><sb:pages><sb:first-page>13</sb:first-page><sb:last-page>23</sb:last-page></sb:pages></sb:host></sb:reference></ce:bib-reference><ce:bib-reference id="bib40"><ce:label>[39]</ce:label><sb:reference><sb:contribution langtype="en"><sb:authors><sb:author><ce:surname>Köhler</ce:surname><ce:given-name>L.</ce:given-name></sb:author><sb:author><ce:surname>Hall</ce:surname><ce:given-name>H.</ce:given-name></sb:author><sb:author><ce:surname>Ogren</ce:surname><ce:given-name>S.V.</ce:given-name></sb:author><sb:author><ce:surname>Gawell</ce:surname><ce:given-name>L.</ce:given-name></sb:author></sb:authors></sb:contribution><sb:host><sb:issue><sb:series><sb:title><sb:maintitle>Biochem. Pharmacol.</sb:maintitle></sb:title><sb:volume-nr>34</sb:volume-nr></sb:series><sb:date>1985</sb:date></sb:issue><sb:pages><sb:first-page>2251</sb:first-page><sb:last-page>2259</sb:last-page></sb:pages></sb:host></sb:reference></ce:bib-reference><ce:bib-reference id="bib41"><ce:label>[40]</ce:label><sb:reference><sb:contribution langtype="en"><sb:authors><sb:author><ce:surname>De Haven-Hudkins</ce:surname><ce:given-name>D.L.</ce:given-name></sb:author><sb:author><ce:surname>Fleissner</ce:surname><ce:given-name>L.C.</ce:given-name></sb:author><sb:author><ce:surname>Ford-Rice</ce:surname><ce:given-name>F.Y.</ce:given-name></sb:author></sb:authors></sb:contribution><sb:host><sb:issue><sb:series><sb:title><sb:maintitle>Eur. J. Pharmacol.</sb:maintitle></sb:title><sb:volume-nr>227</sb:volume-nr></sb:series><sb:date>1992</sb:date></sb:issue><sb:pages><sb:first-page>371</sb:first-page><sb:last-page>378</sb:last-page></sb:pages></sb:host></sb:reference></ce:bib-reference><ce:bib-reference id="bib42"><ce:label>[41]</ce:label><sb:reference><sb:contribution langtype="en"><sb:authors><sb:author><ce:surname>Weber</ce:surname><ce:given-name>E.</ce:given-name></sb:author><sb:author><ce:surname>Sonders</ce:surname><ce:given-name>M.</ce:given-name></sb:author><sb:author><ce:surname>Quarum</ce:surname><ce:given-name>M.</ce:given-name></sb:author><sb:author><ce:surname>McLean</ce:surname><ce:given-name>S.</ce:given-name></sb:author><sb:author><ce:surname>Pou</ce:surname><ce:given-name>S.</ce:given-name></sb:author><sb:author><ce:surname>Keana</ce:surname><ce:given-name>JFW.</ce:given-name></sb:author></sb:authors></sb:contribution><sb:host><sb:edited-book><sb:book-series><sb:series><sb:title><sb:maintitle>Proc. Nat. Acad. Sci USA.</sb:maintitle></sb:title><sb:volume-nr>83</sb:volume-nr></sb:series></sb:book-series><sb:date>1986</sb:date></sb:edited-book><sb:pages><sb:first-page>8784</sb:first-page><sb:last-page>8788</sb:last-page></sb:pages></sb:host><sb:comment>19</sb:comment></sb:reference></ce:bib-reference><ce:bib-reference id="bib43"><ce:label>[42]</ce:label><sb:reference><sb:contribution langtype="en"><sb:authors><sb:author><ce:surname>Monnet</ce:surname><ce:given-name>F.P.</ce:given-name></sb:author><sb:author><ce:surname>Debonnel</ce:surname><ce:given-name>G.</ce:given-name></sb:author><sb:author><ce:surname>De Montigny</ce:surname><ce:given-name>C.</ce:given-name></sb:author></sb:authors></sb:contribution><sb:host><sb:issue><sb:series><sb:title><sb:maintitle>J. Pharmacol. Exp. Ther.</sb:maintitle></sb:title><sb:volume-nr>261</sb:volume-nr></sb:series><sb:date>1992</sb:date></sb:issue><sb:pages><sb:first-page>123</sb:first-page><sb:last-page>130</sb:last-page></sb:pages></sb:host></sb:reference></ce:bib-reference><ce:bib-reference id="bib44"><ce:label>[43]</ce:label><sb:reference><sb:contribution langtype="en"><sb:authors><sb:author><ce:surname>Monnet</ce:surname><ce:given-name>F.P.</ce:given-name></sb:author><sb:author><ce:surname>Debonnel</ce:surname><ce:given-name>G.</ce:given-name></sb:author><sb:author><ce:surname>Junien</ce:surname><ce:given-name>J.L.</ce:given-name></sb:author><sb:author><ce:surname>De Montigny</ce:surname><ce:given-name>C.</ce:given-name></sb:author></sb:authors></sb:contribution><sb:host><sb:issue><sb:series><sb:title><sb:maintitle>Eur. J. Pharmacol.</sb:maintitle></sb:title><sb:volume-nr>179</sb:volume-nr></sb:series><sb:date>1990</sb:date></sb:issue><sb:pages><sb:first-page>441</sb:first-page><sb:last-page>445</sb:last-page></sb:pages></sb:host></sb:reference></ce:bib-reference><ce:bib-reference id="bib45"><ce:label>[44]</ce:label><sb:reference><sb:contribution langtype="en"><sb:authors><sb:author><ce:surname>Costall</ce:surname><ce:given-name>B.</ce:given-name></sb:author><sb:author><ce:surname>Marsden</ce:surname><ce:given-name>C.D.</ce:given-name></sb:author><sb:author><ce:surname>Naylor</ce:surname><ce:given-name>R.J.</ce:given-name></sb:author><sb:author><ce:surname>Pycock</ce:surname><ce:given-name>C.J.</ce:given-name></sb:author></sb:authors></sb:contribution><sb:host><sb:issue><sb:series><sb:title><sb:maintitle>Brain Research</sb:maintitle></sb:title><sb:volume-nr>123</sb:volume-nr></sb:series><sb:date>1977</sb:date></sb:issue><sb:pages><sb:first-page>89</sb:first-page><sb:last-page>111</sb:last-page></sb:pages></sb:host></sb:reference></ce:bib-reference></ce:bibliography-sec></ce:bibliography></tail></article></istex:document></istex:metadataXml><mods version="3.6"><titleInfo lang="en"><title>Synthesis and structure-activity relationships of novel 2-amino alkyl chromones and related derivatives as a site-selective ligands</title></titleInfo><titleInfo type="alternative" lang="en" contentType="CDATA"><title>Synthesis and structure-activity relationships of novel 2-amino alkyl chromones and related derivatives as a site-selective ligands</title></titleInfo><name type="personal"><namePart type="given">Geneviève</namePart><namePart type="family">Baziard-Mouysset</namePart><affiliation>Laboratoire de Chimie Pharmaceutique, Faculté de Pharmacie, 35 Chemin des Maraichers, 31062 Toulouse, France</affiliation><role><roleTerm type="text">author</roleTerm></role></name><name type="personal"><namePart type="given">Salouma</namePart><namePart type="family">Younes</namePart><affiliation>Laboratoire de Chimie Pharmaceutique, Faculté de Pharmacie, 35 Chemin des Maraichers, 31062 Toulouse, France</affiliation><role><roleTerm type="text">author</roleTerm></role></name><name type="personal"><namePart type="given">Youssef</namePart><namePart type="family">Labssita</namePart><affiliation>Laboratoire de Chimie Pharmaceutique, Faculté de Pharmacie, 35 Chemin des Maraichers, 31062 Toulouse, France</affiliation><role><roleTerm type="text">author</roleTerm></role></name><name type="personal"><namePart type="given">Marc</namePart><namePart type="family">Payard</namePart><affiliation>Laboratoire de Chimie Pharmaceutique, Faculté de Pharmacie, 35 Chemin des Maraichers, 31062 Toulouse, France</affiliation><role><roleTerm type="text">author</roleTerm></role></name><name type="personal"><namePart type="given">Daniel-Henri</namePart><namePart type="family">Caignard</namePart><affiliation>Institut de Recherches International Servier, 1 Rue Carle Hébert, 92415 Courbevoie Cedex, France</affiliation><affiliation>Correspondence and reprints.</affiliation><role><roleTerm type="text">author</roleTerm></role></name><name type="personal"><namePart type="given">Marie-Claire</namePart><namePart type="family">Rettori</namePart><affiliation>Institut de Recherches International Servier, 1 Rue Carle Hébert, 92415 Courbevoie Cedex, France</affiliation><role><roleTerm type="text">author</roleTerm></role></name><name type="personal"><namePart type="given">Pierre</namePart><namePart type="family">Renard</namePart><affiliation>Institut de Recherches International Servier, 1 Rue Carle Hébert, 92415 Courbevoie Cedex, France</affiliation><role><roleTerm type="text">author</roleTerm></role></name><name type="personal"><namePart type="given">Bruno</namePart><namePart type="family">Pfeiffer</namePart><affiliation>Institut de Recherches International Servier, 1 Rue Carle Hébert, 92415 Courbevoie Cedex, France</affiliation><role><roleTerm type="text">author</roleTerm></role></name><name type="personal"><namePart type="given">Béatrice</namePart><namePart type="family">Guardiola-Lemaitre</namePart><affiliation>Institut de Recherches International Servier, 1 Rue Carle Hébert, 92415 Courbevoie Cedex, France</affiliation><role><roleTerm type="text">author</roleTerm></role></name><typeOfResource>text</typeOfResource><genre type="research-article" displayLabel="Full-length article"></genre><originInfo><publisher>ELSEVIER</publisher><dateIssued encoding="w3cdtf">1998</dateIssued><copyrightDate encoding="w3cdtf">1998</copyrightDate></originInfo><language><languageTerm type="code" authority="iso639-2b">eng</languageTerm><languageTerm type="code" authority="rfc3066">en</languageTerm></language><physicalDescription><internetMediaType>text/html</internetMediaType></physicalDescription><abstract lang="en">Abstract: Starting from a random screening showing that 2-[(4-benzylpiperazinyl)methyl] chromone was a selective and potent sigma ligand, a series of analogues were synthesized. Introduction of a substituent on the chromone moiety, replacement of methy-lenes by carbonyl groups and benzyl by aryl groups decrease the affinity for sigma sites. The result obtained after introduction of various substituents on the aromatic part of the benzyl is strictly depending on the size and on the position of these substituents. Stretching of the carbon chain between the phenyl and the piperazine does not strongly modify the affinity. 2-[4-(4′-methoxy benzyl)-1-piperazinyl methyl] chromone has been tested in behavioral tests that permit to believe that such derivatives could be interesting for the treatment of psychosis.</abstract><subject lang="en"><topic>sigma ligand</topic><topic>chromone</topic><topic>benzylpiperazine</topic><topic>psychosis</topic></subject><relatedItem type="host"><titleInfo><title>European Journal of Medicinal Chemistry</title></titleInfo><titleInfo type="abbreviated"><title>EJMECH</title></titleInfo><genre type="journal">journal</genre><originInfo><dateIssued encoding="w3cdtf">199806</dateIssued></originInfo><identifier type="ISSN">0223-5234</identifier><identifier type="PII">S0223-5234(00)X0166-3</identifier><part><date>199806</date><detail type="volume"><number>33</number><caption>vol.</caption></detail><detail type="issue"><number>5</number><caption>no.</caption></detail><extent unit="issue pages"><start>339</start><end>420</end></extent><extent unit="pages"><start>339</start><end>347</end></extent></part></relatedItem><identifier type="istex">757D0ADA964638FA3C72A52EFA1A92FB2F265FC5</identifier><identifier type="DOI">10.1016/S0223-5234(98)80001-9</identifier><identifier type="PII">S0223-5234(98)80001-9</identifier><identifier type="ArticleID">98800019</identifier><accessCondition type="use and reproduction" contentType="copyright">©1998 Elsevier, Paris</accessCondition><recordInfo><recordContentSource>ELSEVIER</recordContentSource><recordOrigin>Elsevier, Paris, ©1998</recordOrigin></recordInfo></mods></metadata></istex></record>Pour manipuler ce document sous Unix (Dilib)
EXPLOR_STEP=$WICRI_ROOT/Wicri/Sante/explor/ParkinsonFranceV1/Data/Istex/Corpus
HfdSelect -h $EXPLOR_STEP/biblio.hfd -nk 000D65 | SxmlIndent | more
Ou
HfdSelect -h $EXPLOR_AREA/Data/Istex/Corpus/biblio.hfd -nk 000D65 | SxmlIndent | more
Pour mettre un lien sur cette page dans le réseau Wicri
{{Explor lien
|wiki= Wicri/Sante
|area= ParkinsonFranceV1
|flux= Istex
|étape= Corpus
|type= RBID
|clé= ISTEX:757D0ADA964638FA3C72A52EFA1A92FB2F265FC5
|texte= Synthesis and structure-activity relationships of novel 2-amino alkyl chromones and related derivatives as a site-selective ligands
}}
| This area was generated with Dilib version V0.6.29. |  |