Application of "hydrogen bonding interaction" in new drug development: design, synthesis, antiviral activity, and SARs of thiourea derivatives.
Identifieur interne : 002A19 ( Ncbi/Merge ); précédent : 002A18; suivant : 002A20Application of "hydrogen bonding interaction" in new drug development: design, synthesis, antiviral activity, and SARs of thiourea derivatives.
Auteurs : Aidang Lu [République populaire de Chine] ; Ziwen Wang ; Zhenghong Zhou ; Jianxin Chen ; Qingmin WangSource :
- Journal of agricultural and food chemistry [ 1520-5118 ] ; 2015.
Descripteurs français
- KwdFr :
- MESH :
- pharmacologie : Antiviraux.
- synthèse chimique : Antiviraux.
- virologie : Maladies des plantes, Tabac.
- Antiviraux, Conception de médicament, Liaison hydrogène, Relation structure-activité, Thiourée, Virus de la mosaïque du tabac.
English descriptors
- KwdEn :
- MESH :
- chemical , chemical synthesis : Antiviral Agents.
- chemical , chemistry : Antiviral Agents, Thiourea.
- chemical , pharmacology : Antiviral Agents.
- drug effects : Tobacco Mosaic Virus.
- virology : Plant Diseases, Tobacco.
- Drug Design, Hydrogen Bonding, Structure-Activity Relationship.
Abstract
A series of simple thiourea derivatives were designed based on the structure of natural product harmine and lead compound and synthesized from amines in one step. The antiviral activity of these thiourea derivatives was evaluated. Most of them exhibited significantly higher anti-TMV activity than commercial plant virucides ribavirin, harmine, and lead compound. The hydrogen bond was found to be important but not the more the better. The optimal compound (R,R)-20 showed the best anti-TMV activity in vitro and in vivo (in vitro activity, 75%/500 μg/mL and 39%/100 μg/mL; inactivation activity, 71%/500 μg/mL and 35%/100 μg/mL; curative activity, 73%/500 μg/mL and 37%/100 μg/mL; protection activity, 69%/500 μg/mL and 33%/100 μg/mL), which is significantly higher than that of Ningnanmycin. The systematic study provides strong evidence that these simple thiourea derivatives could become potential TMV inhibitors.
DOI: 10.1021/jf505355r
PubMed: 25619875
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last="Zhou">Zhenghong Zhou</name></author><author><name sortKey="Chen, Jianxin" sort="Chen, Jianxin" uniqKey="Chen J" first="Jianxin" last="Chen">Jianxin Chen</name></author><author><name sortKey="Wang, Qingmin" sort="Wang, Qingmin" uniqKey="Wang Q" first="Qingmin" last="Wang">Qingmin Wang</name></author></titleStmt><publicationStmt><idno type="wicri:source">PubMed</idno><date when="2015">2015</date><idno type="RBID">pubmed:25619875</idno><idno type="pmid">25619875</idno><idno type="doi">10.1021/jf505355r</idno><idno type="wicri:Area/PubMed/Corpus">000E70</idno><idno type="wicri:explorRef" wicri:stream="PubMed" wicri:step="Corpus" wicri:corpus="PubMed">000E70</idno><idno type="wicri:Area/PubMed/Curation">000E70</idno><idno type="wicri:explorRef" wicri:stream="PubMed" wicri:step="Curation">000E70</idno><idno type="wicri:Area/PubMed/Checkpoint">000E56</idno><idno type="wicri:explorRef" wicri:stream="Checkpoint" wicri:step="PubMed">000E56</idno><idno 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uniqKey="Zhou Z" first="Zhenghong" last="Zhou">Zhenghong Zhou</name></author><author><name sortKey="Chen, Jianxin" sort="Chen, Jianxin" uniqKey="Chen J" first="Jianxin" last="Chen">Jianxin Chen</name></author><author><name sortKey="Wang, Qingmin" sort="Wang, Qingmin" uniqKey="Wang Q" first="Qingmin" last="Wang">Qingmin Wang</name></author></analytic><series><title level="j">Journal of agricultural and food chemistry</title><idno type="eISSN">1520-5118</idno><imprint><date when="2015" type="published">2015</date></imprint></series></biblStruct></sourceDesc></fileDesc><profileDesc><textClass><keywords scheme="KwdEn" xml:lang="en"><term>Antiviral Agents (chemical synthesis)</term><term>Antiviral Agents (chemistry)</term><term>Antiviral Agents (pharmacology)</term><term>Drug Design</term><term>Hydrogen Bonding</term><term>Plant Diseases (virology)</term><term>Structure-Activity Relationship</term><term>Thiourea (chemistry)</term><term>Tobacco (virology)</term><term>Tobacco Mosaic Virus (drug effects)</term></keywords><keywords scheme="KwdFr" xml:lang="fr"><term>Antiviraux ()</term><term>Antiviraux (pharmacologie)</term><term>Antiviraux (synthèse chimique)</term><term>Conception de médicament</term><term>Liaison hydrogène</term><term>Maladies des plantes (virologie)</term><term>Relation structure-activité</term><term>Tabac (virologie)</term><term>Thiourée ()</term><term>Virus de la mosaïque du tabac ()</term></keywords><keywords scheme="MESH" type="chemical" qualifier="chemical synthesis" xml:lang="en"><term>Antiviral Agents</term></keywords><keywords scheme="MESH" type="chemical" qualifier="chemistry" xml:lang="en"><term>Antiviral Agents</term><term>Thiourea</term></keywords><keywords scheme="MESH" type="chemical" qualifier="pharmacology" xml:lang="en"><term>Antiviral Agents</term></keywords><keywords scheme="MESH" qualifier="drug effects" xml:lang="en"><term>Tobacco Mosaic Virus</term></keywords><keywords scheme="MESH" qualifier="pharmacologie" xml:lang="fr"><term>Antiviraux</term></keywords><keywords scheme="MESH" qualifier="synthèse chimique" xml:lang="fr"><term>Antiviraux</term></keywords><keywords scheme="MESH" qualifier="virologie" xml:lang="fr"><term>Maladies des plantes</term><term>Tabac</term></keywords><keywords scheme="MESH" qualifier="virology" xml:lang="en"><term>Plant Diseases</term><term>Tobacco</term></keywords><keywords scheme="MESH" xml:lang="en"><term>Drug Design</term><term>Hydrogen Bonding</term><term>Structure-Activity Relationship</term></keywords><keywords scheme="MESH" xml:lang="fr"><term>Antiviraux</term><term>Conception de médicament</term><term>Liaison hydrogène</term><term>Relation structure-activité</term><term>Thiourée</term><term>Virus de la mosaïque du tabac</term></keywords></textClass></profileDesc></teiHeader><front><div type="abstract" xml:lang="en">A series of simple thiourea derivatives were designed based on the structure of natural product harmine and lead compound and synthesized from amines in one step. The antiviral activity of these thiourea derivatives was evaluated. Most of them exhibited significantly higher anti-TMV activity than commercial plant virucides ribavirin, harmine, and lead compound. The hydrogen bond was found to be important but not the more the better. The optimal compound (R,R)-20 showed the best anti-TMV activity in vitro and in vivo (in vitro activity, 75%/500 μg/mL and 39%/100 μg/mL; inactivation activity, 71%/500 μg/mL and 35%/100 μg/mL; curative activity, 73%/500 μg/mL and 37%/100 μg/mL; protection activity, 69%/500 μg/mL and 33%/100 μg/mL), which is significantly higher than that of Ningnanmycin. The systematic study provides strong evidence that these simple thiourea derivatives could become potential TMV inhibitors.</div></front></TEI><pubmed><MedlineCitation Status="MEDLINE" Owner="NLM"><PMID Version="1">25619875</PMID><DateCompleted><Year>2015</Year><Month>09</Month><Day>08</Day></DateCompleted><DateRevised><Year>2015</Year><Month>02</Month><Day>11</Day></DateRevised><Article PubModel="Print-Electronic"><Journal><ISSN IssnType="Electronic">1520-5118</ISSN><JournalIssue CitedMedium="Internet"><Volume>63</Volume><Issue>5</Issue><PubDate><Year>2015</Year><Month>Feb</Month><Day>11</Day></PubDate></JournalIssue><Title>Journal of agricultural and food chemistry</Title><ISOAbbreviation>J. Agric. Food Chem.</ISOAbbreviation></Journal><ArticleTitle>Application of "hydrogen bonding interaction" in new drug development: design, synthesis, antiviral activity, and SARs of thiourea derivatives.</ArticleTitle><Pagination><MedlinePgn>1378-84</MedlinePgn></Pagination><ELocationID EIdType="doi" ValidYN="Y">10.1021/jf505355r</ELocationID><Abstract><AbstractText>A series of simple thiourea derivatives were designed based on the structure of natural product harmine and lead compound and synthesized from amines in one step. The antiviral activity of these thiourea derivatives was evaluated. Most of them exhibited significantly higher anti-TMV activity than commercial plant virucides ribavirin, harmine, and lead compound. The hydrogen bond was found to be important but not the more the better. The optimal compound (R,R)-20 showed the best anti-TMV activity in vitro and in vivo (in vitro activity, 75%/500 μg/mL and 39%/100 μg/mL; inactivation activity, 71%/500 μg/mL and 35%/100 μg/mL; curative activity, 73%/500 μg/mL and 37%/100 μg/mL; protection activity, 69%/500 μg/mL and 33%/100 μg/mL), which is significantly higher than that of Ningnanmycin. The systematic study provides strong evidence that these simple thiourea derivatives could become potential TMV inhibitors.</AbstractText></Abstract><AuthorList CompleteYN="Y"><Author ValidYN="Y"><LastName>Lu</LastName><ForeName>Aidang</ForeName><Initials>A</Initials><AffiliationInfo><Affiliation>School of Marine Science and Engineering, Hebei University of Technology , Tianjin 300130, China.</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>Wang</LastName><ForeName>Ziwen</ForeName><Initials>Z</Initials></Author><Author ValidYN="Y"><LastName>Zhou</LastName><ForeName>Zhenghong</ForeName><Initials>Z</Initials></Author><Author ValidYN="Y"><LastName>Chen</LastName><ForeName>Jianxin</ForeName><Initials>J</Initials></Author><Author ValidYN="Y"><LastName>Wang</LastName><ForeName>Qingmin</ForeName><Initials>Q</Initials></Author></AuthorList><Language>eng</Language><PublicationTypeList><PublicationType UI="D016428">Journal Article</PublicationType><PublicationType UI="D013485">Research Support, Non-U.S. Gov't</PublicationType></PublicationTypeList><ArticleDate DateType="Electronic"><Year>2015</Year><Month>02</Month><Day>03</Day></ArticleDate></Article><MedlineJournalInfo><Country>United States</Country><MedlineTA>J Agric Food Chem</MedlineTA><NlmUniqueID>0374755</NlmUniqueID><ISSNLinking>0021-8561</ISSNLinking></MedlineJournalInfo><ChemicalList><Chemical><RegistryNumber>0</RegistryNumber><NameOfSubstance UI="D000998">Antiviral Agents</NameOfSubstance></Chemical><Chemical><RegistryNumber>GYV9AM2QAG</RegistryNumber><NameOfSubstance UI="D013890">Thiourea</NameOfSubstance></Chemical></ChemicalList><CitationSubset>IM</CitationSubset><MeshHeadingList><MeshHeading><DescriptorName UI="D000998" MajorTopicYN="N">Antiviral Agents</DescriptorName><QualifierName UI="Q000138" MajorTopicYN="Y">chemical synthesis</QualifierName><QualifierName UI="Q000737" MajorTopicYN="N">chemistry</QualifierName><QualifierName UI="Q000494" MajorTopicYN="Y">pharmacology</QualifierName></MeshHeading><MeshHeading><DescriptorName UI="D015195" MajorTopicYN="N">Drug Design</DescriptorName></MeshHeading><MeshHeading><DescriptorName UI="D006860" MajorTopicYN="N">Hydrogen Bonding</DescriptorName></MeshHeading><MeshHeading><DescriptorName UI="D010935" MajorTopicYN="N">Plant Diseases</DescriptorName><QualifierName UI="Q000821" MajorTopicYN="N">virology</QualifierName></MeshHeading><MeshHeading><DescriptorName UI="D013329" MajorTopicYN="N">Structure-Activity Relationship</DescriptorName></MeshHeading><MeshHeading><DescriptorName UI="D013890" MajorTopicYN="N">Thiourea</DescriptorName><QualifierName UI="Q000737" MajorTopicYN="Y">chemistry</QualifierName></MeshHeading><MeshHeading><DescriptorName UI="D014026" MajorTopicYN="N">Tobacco</DescriptorName><QualifierName UI="Q000821" MajorTopicYN="N">virology</QualifierName></MeshHeading><MeshHeading><DescriptorName UI="D014027" MajorTopicYN="N">Tobacco Mosaic Virus</DescriptorName><QualifierName UI="Q000187" MajorTopicYN="N">drug effects</QualifierName></MeshHeading></MeshHeadingList><KeywordList Owner="NOTNLM"><Keyword MajorTopicYN="N">SARs</Keyword><Keyword MajorTopicYN="N">anti-TMV activity</Keyword><Keyword MajorTopicYN="N">nature product</Keyword><Keyword MajorTopicYN="N">thiourea derivatives</Keyword><Keyword MajorTopicYN="N">tobacco mosaic virus</Keyword></KeywordList></MedlineCitation><PubmedData><History><PubMedPubDate PubStatus="entrez"><Year>2015</Year><Month>1</Month><Day>27</Day><Hour>6</Hour><Minute>0</Minute></PubMedPubDate><PubMedPubDate PubStatus="pubmed"><Year>2015</Year><Month>1</Month><Day>27</Day><Hour>6</Hour><Minute>0</Minute></PubMedPubDate><PubMedPubDate PubStatus="medline"><Year>2015</Year><Month>9</Month><Day>9</Day><Hour>6</Hour><Minute>0</Minute></PubMedPubDate></History><PublicationStatus>ppublish</PublicationStatus><ArticleIdList><ArticleId IdType="pubmed">25619875</ArticleId><ArticleId IdType="doi">10.1021/jf505355r</ArticleId></ArticleIdList></PubmedData></pubmed><affiliations><list><country><li>République populaire de Chine</li></country><settlement><li>Tianjin</li></settlement></list><tree><noCountry><name sortKey="Chen, Jianxin" sort="Chen, Jianxin" uniqKey="Chen J" first="Jianxin" last="Chen">Jianxin Chen</name><name sortKey="Wang, Qingmin" sort="Wang, Qingmin" uniqKey="Wang Q" first="Qingmin" last="Wang">Qingmin Wang</name><name sortKey="Wang, Ziwen" sort="Wang, Ziwen" uniqKey="Wang Z" first="Ziwen" last="Wang">Ziwen Wang</name><name sortKey="Zhou, Zhenghong" sort="Zhou, Zhenghong" uniqKey="Zhou Z" first="Zhenghong" last="Zhou">Zhenghong Zhou</name></noCountry><country name="République populaire de Chine"><noRegion><name sortKey="Lu, Aidang" sort="Lu, Aidang" uniqKey="Lu A" first="Aidang" last="Lu">Aidang Lu</name></noRegion></country></tree></affiliations></record>Pour manipuler ce document sous Unix (Dilib)
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