SrasV1, Main, Exploration, bibRecord, 001700

Arylazolyl(azinyl)thioacetanilides. Part 16: Structure-based bioisosterism design, synthesis and biological evaluation of novel pyrimidinylthioacetanilides as potent HIV-1 inhibitors.

Identifieur interne : 001700 ( Main/Exploration ); précédent : 001699; suivant : 001701

Arylazolyl(azinyl)thioacetanilides. Part 16: Structure-based bioisosterism design, synthesis and biological evaluation of novel pyrimidinylthioacetanilides as potent HIV-1 inhibitors.

Auteurs : Xiao Li [République populaire de Chine] ; Xueyi Lu [République populaire de Chine] ; Wenmin Chen [République populaire de Chine] ; Huiqing Liu [République populaire de Chine] ; Peng Zhan [République populaire de Chine] ; Christophe Pannecouque [Belgique] ; Jan Balzarini [Belgique] ; Erik De Clercq [Belgique] ; Xinyong Liu [République populaire de Chine]

Source :

Bioorganic & medicinal chemistry [ 1464-3391 ] ; 2014.

RBID : pubmed:25150090

Descripteurs français

KwdFr :
- Acétanilides (), Acétanilides (pharmacologie), Acétanilides (synthèse chimique), Agents antiVIH (), Agents antiVIH (pharmacologie), Agents antiVIH (synthèse chimique), Conception de médicament, Modèles moléculaires, Pyrimidines (), Pyrimidines (pharmacologie), Pyrimidines (synthèse chimique), Relation dose-effet des médicaments, Relation structure-activité, Réplication virale (), Structure moléculaire, Tests de sensibilité microbienne, VIH-1 (Virus de l'Immunodéficience Humaine de type 1) (), VIH-1 (Virus de l'Immunodéficience Humaine de type 1) (croissance et développement).
MESH :
- croissance et développement : VIH-1 (Virus de l'Immunodéficience Humaine de type 1).
- pharmacologie : Acétanilides, Agents antiVIH, Pyrimidines.
- synthèse chimique : Acétanilides, Agents antiVIH, Pyrimidines.
- Acétanilides, Agents antiVIH, Conception de médicament, Modèles moléculaires, Pyrimidines, Relation dose-effet des médicaments, Relation structure-activité, Réplication virale, Structure moléculaire, Tests de sensibilité microbienne, VIH-1 (Virus de l'Immunodéficience Humaine de type 1).

English descriptors

KwdEn :
- Acetanilides (chemical synthesis), Acetanilides (chemistry), Acetanilides (pharmacology), Anti-HIV Agents (chemical synthesis), Anti-HIV Agents (chemistry), Anti-HIV Agents (pharmacology), Dose-Response Relationship, Drug, Drug Design, HIV-1 (drug effects), HIV-1 (growth & development), Microbial Sensitivity Tests, Models, Molecular, Molecular Structure, Pyrimidines (chemical synthesis), Pyrimidines (chemistry), Pyrimidines (pharmacology), Structure-Activity Relationship, Virus Replication (drug effects).
MESH :
- chemical , chemical synthesis : Acetanilides, Anti-HIV Agents, Pyrimidines.
- chemical , chemistry : Acetanilides, Anti-HIV Agents, Pyrimidines.
- chemical , pharmacology : Acetanilides, Anti-HIV Agents, Pyrimidines.
- drug effects : HIV-1, Virus Replication.
- growth & development : HIV-1.
- Dose-Response Relationship, Drug, Drug Design, Microbial Sensitivity Tests, Models, Molecular, Molecular Structure, Structure-Activity Relationship.

Abstract

A series of novel pyrimidinylthioacetanilides were designed, synthesized, and evaluated for their biological activity as potent HIV-1 non-nucleoside reverse transcriptase inhibitors (NNRTIs). Most of the tested compounds were proved to be effective in inhibiting HIV-1 (IIIB) replication with EC50 ranging from 0.15 μM to 24.2 μM, thereinto compound 15 was the most active lead with favorable inhibitory activity against HIV-1 (IIIB) (EC50=0.15 μM, SI=684). Besides, compound 6 displayed moderate inhibition against the double-mutated HIV-1 strain (K103N/Y181C) (EC50=3.9 μM). Preliminary structure-activity relationships (SARs), structure-cytotoxicity relationships (SCRs) data, and molecular modeling studies were discussed as well, which may provide valuable insights for further optimizations.

DOI: 10.1016/j.bmc.2014.08.001
PubMed: 25150090

Affiliations:

Belgique, République populaire de Chine

Le document en format XML

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<wicri:noRegion>Shandong</wicri:noRegion>
</affiliation>
</author>
<author><name sortKey="Zhan, Peng" sort="Zhan, Peng" uniqKey="Zhan P" first="Peng" last="Zhan">Peng Zhan</name>
<affiliation wicri:level="1"><nlm:affiliation>Department of Medicinal Chemistry, School of Pharmaceutical Sciences, Shandong University, 44, West Culture Road, 250012 Jinan, Shandong, PR China. Electronic address: zhanpeng1982@sdu.edu.cn.</nlm:affiliation>
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<profileDesc><textClass><keywords scheme="KwdEn" xml:lang="en"><term>Acetanilides (chemical synthesis)</term>
<term>Acetanilides (chemistry)</term>
<term>Acetanilides (pharmacology)</term>
<term>Anti-HIV Agents (chemical synthesis)</term>
<term>Anti-HIV Agents (chemistry)</term>
<term>Anti-HIV Agents (pharmacology)</term>
<term>Dose-Response Relationship, Drug</term>
<term>Drug Design</term>
<term>HIV-1 (drug effects)</term>
<term>HIV-1 (growth & development)</term>
<term>Microbial Sensitivity Tests</term>
<term>Models, Molecular</term>
<term>Molecular Structure</term>
<term>Pyrimidines (chemical synthesis)</term>
<term>Pyrimidines (chemistry)</term>
<term>Pyrimidines (pharmacology)</term>
<term>Structure-Activity Relationship</term>
<term>Virus Replication (drug effects)</term>
</keywords>
<keywords scheme="KwdFr" xml:lang="fr"><term>Acétanilides ()</term>
<term>Acétanilides (pharmacologie)</term>
<term>Acétanilides (synthèse chimique)</term>
<term>Agents antiVIH ()</term>
<term>Agents antiVIH (pharmacologie)</term>
<term>Agents antiVIH (synthèse chimique)</term>
<term>Conception de médicament</term>
<term>Modèles moléculaires</term>
<term>Pyrimidines ()</term>
<term>Pyrimidines (pharmacologie)</term>
<term>Pyrimidines (synthèse chimique)</term>
<term>Relation dose-effet des médicaments</term>
<term>Relation structure-activité</term>
<term>Réplication virale ()</term>
<term>Structure moléculaire</term>
<term>Tests de sensibilité microbienne</term>
<term>VIH-1 (Virus de l'Immunodéficience Humaine de type 1) ()</term>
<term>VIH-1 (Virus de l'Immunodéficience Humaine de type 1) (croissance et développement)</term>
</keywords>
<keywords scheme="MESH" type="chemical" qualifier="chemical synthesis" xml:lang="en"><term>Acetanilides</term>
<term>Anti-HIV Agents</term>
<term>Pyrimidines</term>
</keywords>
<keywords scheme="MESH" type="chemical" qualifier="chemistry" xml:lang="en"><term>Acetanilides</term>
<term>Anti-HIV Agents</term>
<term>Pyrimidines</term>
</keywords>
<keywords scheme="MESH" type="chemical" qualifier="pharmacology" xml:lang="en"><term>Acetanilides</term>
<term>Anti-HIV Agents</term>
<term>Pyrimidines</term>
</keywords>
<keywords scheme="MESH" qualifier="croissance et développement" xml:lang="fr"><term>VIH-1 (Virus de l'Immunodéficience Humaine de type 1)</term>
</keywords>
<keywords scheme="MESH" qualifier="drug effects" xml:lang="en"><term>HIV-1</term>
<term>Virus Replication</term>
</keywords>
<keywords scheme="MESH" qualifier="growth & development" xml:lang="en"><term>HIV-1</term>
</keywords>
<keywords scheme="MESH" qualifier="pharmacologie" xml:lang="fr"><term>Acétanilides</term>
<term>Agents antiVIH</term>
<term>Pyrimidines</term>
</keywords>
<keywords scheme="MESH" qualifier="synthèse chimique" xml:lang="fr"><term>Acétanilides</term>
<term>Agents antiVIH</term>
<term>Pyrimidines</term>
</keywords>
<keywords scheme="MESH" xml:lang="en"><term>Dose-Response Relationship, Drug</term>
<term>Drug Design</term>
<term>Microbial Sensitivity Tests</term>
<term>Models, Molecular</term>
<term>Molecular Structure</term>
<term>Structure-Activity Relationship</term>
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<term>Agents antiVIH</term>
<term>Conception de médicament</term>
<term>Modèles moléculaires</term>
<term>Pyrimidines</term>
<term>Relation dose-effet des médicaments</term>
<term>Relation structure-activité</term>
<term>Réplication virale</term>
<term>Structure moléculaire</term>
<term>Tests de sensibilité microbienne</term>
<term>VIH-1 (Virus de l'Immunodéficience Humaine de type 1)</term>
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<front><div type="abstract" xml:lang="en">A series of novel pyrimidinylthioacetanilides were designed, synthesized, and evaluated for their biological activity as potent HIV-1 non-nucleoside reverse transcriptase inhibitors (NNRTIs). Most of the tested compounds were proved to be effective in inhibiting HIV-1 (IIIB) replication with EC50 ranging from 0.15 μM to 24.2 μM, thereinto compound 15 was the most active lead with favorable inhibitory activity against HIV-1 (IIIB) (EC50=0.15 μM, SI=684). Besides, compound 6 displayed moderate inhibition against the double-mutated HIV-1 strain (K103N/Y181C) (EC50=3.9 μM). Preliminary structure-activity relationships (SARs), structure-cytotoxicity relationships (SCRs) data, and molecular modeling studies were discussed as well, which may provide valuable insights for further optimizations.</div>
</front>
</TEI>
<affiliations><list><country><li>Belgique</li>
<li>République populaire de Chine</li>
</country>
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<name sortKey="Liu, Huiqing" sort="Liu, Huiqing" uniqKey="Liu H" first="Huiqing" last="Liu">Huiqing Liu</name>
<name sortKey="Liu, Xinyong" sort="Liu, Xinyong" uniqKey="Liu X" first="Xinyong" last="Liu">Xinyong Liu</name>
<name sortKey="Lu, Xueyi" sort="Lu, Xueyi" uniqKey="Lu X" first="Xueyi" last="Lu">Xueyi Lu</name>
<name sortKey="Zhan, Peng" sort="Zhan, Peng" uniqKey="Zhan P" first="Peng" last="Zhan">Peng Zhan</name>
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<name sortKey="De Clercq, Erik" sort="De Clercq, Erik" uniqKey="De Clercq E" first="Erik" last="De Clercq">Erik De Clercq</name>
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Arylazolyl(azinyl)thioacetanilides. Part 16: Structure-based bioisosterism design, synthesis and biological evaluation of novel pyrimidinylthioacetanilides as potent HIV-1 inhibitors.

Arylazolyl(azinyl)thioacetanilides. Part 16: Structure-based bioisosterism design, synthesis and biological evaluation of novel pyrimidinylthioacetanilides as potent HIV-1 inhibitors.

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