5-Substituted 2-amino-4,6-dihydroxypyrimidines and 2-amino-4,6-dichloropyrimidines: synthesis and inhibitory effects on immune-activated nitric oxide production
Identifieur interne : 001195 ( Main/Exploration ); précédent : 001194; suivant : 0011965-Substituted 2-amino-4,6-dihydroxypyrimidines and 2-amino-4,6-dichloropyrimidines: synthesis and inhibitory effects on immune-activated nitric oxide production
Auteurs : Petr Jansa [République tchèque] ; Antonín Hol [République tchèque] ; Martin Dra Nsk [République tchèque] ; Viktor Kolman [République tchèque] ; Zlatko Janeba [République tchèque] ; Petra Kostecká [République tchèque] ; Eva Kmoní Ková [République tchèque] ; Zden K Zídek [République tchèque]Source :
- Medicinal Chemistry Research [ 1054-2523 ] ; 2014.
Abstract
A series of 5-substituted 2-amino-4,6-dihydroxypyrimidines were prepared by a modified condensation of the corresponding monosubstituted malonic acid diesters with guanidine in an excess of sodium ethoxide. The optimized procedure using Vilsmeier–Haack–Arnold reagent, followed by immediate deprotection of the (dimethylamino)methylene protecting groups, has been developed to convert the 2-amino-4,6-dihydroxypyrimidine analogs to novel 5-substituted 2-amino-4,6-dichloropyrimidines in high yields. Pilot screening for biological properties of the prepared compounds was done in mouse peritoneal cells using the in vitro nitric oxide (NO) assay. Irrespective of the substituent at the 5 position, 2-amino-4,6-dichloropyrimidines inhibited immune-activated NO production. The most effective was 5-fluoro-2-amino-4,6-dichloropyrimidine with an
Url:
DOI: 10.1007/s00044-014-1018-9
PubMed: NONE
PubMed Central: 7080047
Affiliations:
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Republic,</institution></institution-wrap>Vídeňská 1083, 142 20 Prague 4, Czech Republic</nlm:aff><country xml:lang="fr">République tchèque</country><wicri:regionArea>Vídeňská 1083, 142 20 Prague 4</wicri:regionArea><wicri:noRegion>142 20 Prague 4</wicri:noRegion></affiliation></author></analytic><series><title level="j">Medicinal Chemistry Research</title><idno type="ISSN">1054-2523</idno><idno type="eISSN">1554-8120</idno><imprint><date when="2014">2014</date></imprint></series></biblStruct></sourceDesc></fileDesc><profileDesc><textClass></textClass></profileDesc></teiHeader><front><div type="abstract" xml:lang="en"><p>A series of 5-substituted 2-amino-4,6-dihydroxypyrimidines were prepared by a modified condensation of the corresponding monosubstituted malonic acid diesters with guanidine in an excess of sodium ethoxide. The optimized procedure using Vilsmeier–Haack–Arnold reagent, followed by immediate deprotection of the (dimethylamino)methylene protecting groups, has been developed to convert the 2-amino-4,6-dihydroxypyrimidine analogs to novel 5-substituted 2-amino-4,6-dichloropyrimidines in high yields. Pilot screening for biological properties of the prepared compounds was done in mouse peritoneal cells using the in vitro nitric oxide (NO) assay. Irrespective of the substituent at the 5 position, 2-amino-4,6-dichloropyrimidines inhibited immune-activated NO production. The most effective was 5-fluoro-2-amino-4,6-dichloropyrimidine with an <italic>IC</italic><sub>50</sub> of 2 µM (higher activity than the most potent reference compound) while the <italic>IC</italic><sub>50</sub>s of other derivatives were within the range of 9–36 µM. The 2-amino-4,6-dihydroxypyrimidine counterparts were devoid of any NO-inhibitory activity. The compounds had no suppressive effects on the viability of cells. The Mechanism of action remains to be elucidated.</p></div></front><back><div1 type="bibliography"><listBibl><biblStruct><analytic><author><name sortKey="Altenbach, Rj" uniqKey="Altenbach R">RJ Altenbach</name></author><author><name sortKey="Adair, Rm" uniqKey="Adair R">RM Adair</name></author><author><name sortKey="Bettencourt, Bm" uniqKey="Bettencourt B">BM Bettencourt</name></author><author><name sortKey="Black, La" uniqKey="Black L">LA Black</name></author><author><name sortKey="Fix Stenzel, Sr" uniqKey="Fix Stenzel S">SR Fix-Stenzel</name></author><author><name sortKey="Gopalakrishnan, Sm" uniqKey="Gopalakrishnan S">SM Gopalakrishnan</name></author><author><name sortKey="Hsieh, Gc" uniqKey="Hsieh G">GC Hsieh</name></author><author><name sortKey="Liu, Hq" uniqKey="Liu H">HQ Liu</name></author><author><name sortKey="Marsh, Kc" uniqKey="Marsh K">KC Marsh</name></author><author><name sortKey="Mcpherson, Mj" uniqKey="Mcpherson M">MJ McPherson</name></author><author><name 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uniqKey="De Clercq E">E De Clercq</name></author><author><name sortKey="Neyts, J" uniqKey="Neyts J">J Neyts</name></author></analytic></biblStruct></listBibl></div1></back></TEI><affiliations><list><country><li>République tchèque</li></country></list><tree><country name="République tchèque"><noRegion><name sortKey="Jansa, Petr" sort="Jansa, Petr" uniqKey="Jansa P" first="Petr" last="Jansa">Petr Jansa</name></noRegion><name sortKey="Dra Nsk, Martin" sort="Dra Nsk, Martin" uniqKey="Dra Nsk M" first="Martin" last="Dra Nsk">Martin Dra Nsk</name><name sortKey="Hol, Antonin" sort="Hol, Antonin" uniqKey="Hol A" first="Antonín" last="Hol">Antonín Hol</name><name sortKey="Janeba, Zlatko" sort="Janeba, Zlatko" uniqKey="Janeba Z" first="Zlatko" last="Janeba">Zlatko Janeba</name><name sortKey="Kmoni Kova, Eva" sort="Kmoni Kova, Eva" uniqKey="Kmoni Kova E" first="Eva" last="Kmoní Ková">Eva Kmoní Ková</name><name sortKey="Kmoni Kova, Eva" sort="Kmoni Kova, Eva" uniqKey="Kmoni Kova E" first="Eva" last="Kmoní Ková">Eva Kmoní Ková</name><name sortKey="Kolman, Viktor" sort="Kolman, Viktor" uniqKey="Kolman V" first="Viktor" last="Kolman">Viktor Kolman</name><name sortKey="Kostecka, Petra" sort="Kostecka, Petra" uniqKey="Kostecka P" first="Petra" last="Kostecká">Petra Kostecká</name><name sortKey="Zidek, Zden K" sort="Zidek, Zden K" uniqKey="Zidek Z" first="Zden K" last="Zídek">Zden K Zídek</name></country></tree></affiliations></record>Pour manipuler ce document sous Unix (Dilib)
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