SrasV1, Main, Exploration, bibRecord, 001661

Discovery of novel diarylpyrimidines as potent HIV NNRTIs via a structure-guided core-refining approach.

Identifieur interne : 001661 ( Main/Exploration ); précédent : 001660; suivant : 001662

Discovery of novel diarylpyrimidines as potent HIV NNRTIs via a structure-guided core-refining approach.

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

Source :

European journal of medicinal chemistry [ 1768-3254 ] ; 2014.

RBID : pubmed:24769349

Descripteurs français

English descriptors

KwdEn :
- Drug Design, HIV Reverse Transcriptase (antagonists & inhibitors), HIV Reverse Transcriptase (chemistry), HIV Reverse Transcriptase (metabolism), HIV-1 (drug effects), HIV-1 (enzymology), HIV-1 (physiology), Molecular Docking Simulation, Protein Conformation, Pyrimidines (chemistry), Pyrimidines (metabolism), Pyrimidines (pharmacology), Reverse Transcriptase Inhibitors (chemistry), Reverse Transcriptase Inhibitors (metabolism), Reverse Transcriptase Inhibitors (pharmacology), Structure-Activity Relationship, Virus Replication (drug effects).
MESH :
- chemical , antagonists & inhibitors : HIV Reverse Transcriptase.
- chemical , chemistry : HIV Reverse Transcriptase, Pyrimidines, Reverse Transcriptase Inhibitors.
- chemical , metabolism : HIV Reverse Transcriptase, Pyrimidines, Reverse Transcriptase Inhibitors.
- drug effects : HIV-1, Virus Replication.
- enzymology : HIV-1.
- chemical , pharmacology : Pyrimidines, Reverse Transcriptase Inhibitors.
- physiology : HIV-1.
- Drug Design, Molecular Docking Simulation, Protein Conformation, Structure-Activity Relationship.

Abstract

Guided by crystal structures of HIV-1 RT/DAPY complex and molecular modeling studies, a series of novel DAPY derivatives were rationally designed, synthesized and evaluated for their anti-HIV activities. Among them, 16 compounds significantly inhibited HIV-1 IIIB replication with EC50 values lower than 66 nM. Particularly, compound 7a was the most potent inhibitor against HIV-1 wild-type and double RT mutant HIV-1 strain K103N/Y181C, with an EC50 value of 2.5 nM (SI = 13,740) and 0.33 μM (SI = 107), respectively. Unexpectedly, compound 8c was found to show moderate anti-HIV-2 potency (EC50 = 5.57 μM). Preliminary structure-activity relationships (SARs) and molecular modeling of these new analogues were also discussed in detail.

DOI: 10.1016/j.ejmech.2014.04.036
PubMed: 24769349

Affiliations:

Belgique, République populaire de Chine

Le document en format XML

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<term>HIV Reverse Transcriptase (metabolism)</term>
<term>HIV-1 (drug effects)</term>
<term>HIV-1 (enzymology)</term>
<term>HIV-1 (physiology)</term>
<term>Molecular Docking Simulation</term>
<term>Protein Conformation</term>
<term>Pyrimidines (chemistry)</term>
<term>Pyrimidines (metabolism)</term>
<term>Pyrimidines (pharmacology)</term>
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<term>Reverse Transcriptase Inhibitors (metabolism)</term>
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<term>Conformation des protéines</term>
<term>Inhibiteurs de la transcriptase inverse ()</term>
<term>Inhibiteurs de la transcriptase inverse (métabolisme)</term>
<term>Inhibiteurs de la transcriptase inverse (pharmacologie)</term>
<term>Pyrimidines ()</term>
<term>Pyrimidines (métabolisme)</term>
<term>Pyrimidines (pharmacologie)</term>
<term>Relation structure-activité</term>
<term>Réplication virale ()</term>
<term>Simulation de docking moléculaire</term>
<term>Transcriptase inverse du VIH ()</term>
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<term>Transcriptase inverse du VIH (métabolisme)</term>
<term>VIH-1 (Virus de l'Immunodéficience Humaine de type 1) ()</term>
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<term>VIH-1 (Virus de l'Immunodéficience Humaine de type 1) (physiologie)</term>
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<keywords scheme="MESH" type="chemical" qualifier="antagonists & inhibitors" xml:lang="en"><term>HIV Reverse Transcriptase</term>
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<keywords scheme="MESH" type="chemical" qualifier="chemistry" xml:lang="en"><term>HIV Reverse Transcriptase</term>
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<front><div type="abstract" xml:lang="en">Guided by crystal structures of HIV-1 RT/DAPY complex and molecular modeling studies, a series of novel DAPY derivatives were rationally designed, synthesized and evaluated for their anti-HIV activities. Among them, 16 compounds significantly inhibited HIV-1 IIIB replication with EC50 values lower than 66 nM. Particularly, compound 7a was the most potent inhibitor against HIV-1 wild-type and double RT mutant HIV-1 strain K103N/Y181C, with an EC50 value of 2.5 nM (SI = 13,740) and 0.33 μM (SI = 107), respectively. Unexpectedly, compound 8c was found to show moderate anti-HIV-2 potency (EC50 = 5.57 μM). Preliminary structure-activity relationships (SARs) and molecular modeling of these new analogues were also discussed in detail.</div>
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Discovery of novel diarylpyrimidines as potent HIV NNRTIs via a structure-guided core-refining approach.

Discovery of novel diarylpyrimidines as potent HIV NNRTIs via a structure-guided core-refining approach.

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