Indazolyl-substituted piperidin-4-yl-aminopyrimidines as HIV-1 NNRTIs: Design, synthesis and biological activities.
Identifieur interne : 000857 ( PubMed/Corpus ); précédent : 000856; suivant : 000858Indazolyl-substituted piperidin-4-yl-aminopyrimidines as HIV-1 NNRTIs: Design, synthesis and biological activities.
Auteurs : Ting Xiao ; Jia-Fan Tang ; Ge Meng ; Christophe Pannecouque ; Yuan-Yuan Zhu ; Gen-Yan Liu ; Zhi-Qiang Xu ; Feng-Shou Wu ; Shuang-Xi Gu ; Fen-Er ChenSource :
- European journal of medicinal chemistry [ 1768-3254 ] ; 2020.
English descriptors
- KwdEn :
- Anti-HIV Agents (chemical synthesis), Anti-HIV Agents (chemistry), Anti-HIV Agents (pharmacology), Dose-Response Relationship, Drug, Drug Design, HIV (drug effects), HIV Reverse Transcriptase (antagonists & inhibitors), HIV Reverse Transcriptase (metabolism), Humans, Indazoles (chemistry), Indazoles (pharmacology), Microbial Sensitivity Tests, Molecular Structure, Piperidines (chemical synthesis), Piperidines (chemistry), Piperidines (pharmacology), Pyrimidines (chemical synthesis), Pyrimidines (chemistry), Pyrimidines (pharmacology), Reverse Transcriptase Inhibitors (chemical synthesis), Reverse Transcriptase Inhibitors (chemistry), Reverse Transcriptase Inhibitors (pharmacology), Structure-Activity Relationship.
- MESH :
- chemical , antagonists & inhibitors : HIV Reverse Transcriptase.
- chemical , chemical synthesis : Anti-HIV Agents, Piperidines, Pyrimidines, Reverse Transcriptase Inhibitors.
- chemical , chemistry : Anti-HIV Agents, Indazoles, Piperidines, Pyrimidines, Reverse Transcriptase Inhibitors.
- chemical , metabolism : HIV Reverse Transcriptase.
- chemical , pharmacology : Anti-HIV Agents, Indazoles, Piperidines, Pyrimidines, Reverse Transcriptase Inhibitors.
- drug effects : HIV.
- Dose-Response Relationship, Drug, Drug Design, Humans, Microbial Sensitivity Tests, Molecular Structure, Structure-Activity Relationship.
Abstract
A series of indazolyl-substituted piperidin-4-yl-aminopyrimidines (IPAPYs) were designed from two potent HIV-1 NNRTIs piperidin-4-yl-aminopyrimidine 3c and diaryl ether 4 as the lead compounds by molecular hybridization strategy. The target molecules 5a-q were synthesized and evaluated for their anti-HIV activities and cytotoxicities in MT-4 cells. 5a-q displayed moderate to excellent activities against wild-type (WT) HIV-1 with EC50 values ranging from 1.5 to 0.0064 μM. Among them, 5q was regarded as the most excellent compound against WT HIV-1 (EC50 = 6.4 nM, SI = 2500). And also, it displayed potent activities against K103 N (EC50 = 0.077 μM), Y181C (EC50 = 0.11 μM), E138K (EC50 = 0.057 μM), and moderate activity against double mutants RES056 (EC50 = 8.7 μM). Moreover, the structure-activity relationships (SARs) were summarized, and the molecular docking was performed to investigate the binding mode of IPAPYs and HIV-1 reverse transcriptase.
DOI: 10.1016/j.ejmech.2019.111864
PubMed: 31767136
Links to Exploration step
pubmed:31767136Le document en format XML
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<term>Drug Design</term>
<term>HIV (drug effects)</term>
<term>HIV Reverse Transcriptase (antagonists & inhibitors)</term>
<term>HIV Reverse Transcriptase (metabolism)</term>
<term>Humans</term>
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<front><div type="abstract" xml:lang="en">A series of indazolyl-substituted piperidin-4-yl-aminopyrimidines (IPAPYs) were designed from two potent HIV-1 NNRTIs piperidin-4-yl-aminopyrimidine 3c and diaryl ether 4 as the lead compounds by molecular hybridization strategy. The target molecules 5a-q were synthesized and evaluated for their anti-HIV activities and cytotoxicities in MT-4 cells. 5a-q displayed moderate to excellent activities against wild-type (WT) HIV-1 with EC<sub>50</sub>
values ranging from 1.5 to 0.0064 μM. Among them, 5q was regarded as the most excellent compound against WT HIV-1 (EC<sub>50</sub>
= 6.4 nM, SI = 2500). And also, it displayed potent activities against K103 N (EC<sub>50</sub>
= 0.077 μM), Y181C (EC<sub>50</sub>
= 0.11 μM), E138K (EC<sub>50</sub>
= 0.057 μM), and moderate activity against double mutants RES056 (EC<sub>50</sub>
= 8.7 μM). Moreover, the structure-activity relationships (SARs) were summarized, and the molecular docking was performed to investigate the binding mode of IPAPYs and HIV-1 reverse transcriptase.</div>
</front>
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<ArticleTitle>Indazolyl-substituted piperidin-4-yl-aminopyrimidines as HIV-1 NNRTIs: Design, synthesis and biological activities.</ArticleTitle>
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<Abstract><AbstractText>A series of indazolyl-substituted piperidin-4-yl-aminopyrimidines (IPAPYs) were designed from two potent HIV-1 NNRTIs piperidin-4-yl-aminopyrimidine 3c and diaryl ether 4 as the lead compounds by molecular hybridization strategy. The target molecules 5a-q were synthesized and evaluated for their anti-HIV activities and cytotoxicities in MT-4 cells. 5a-q displayed moderate to excellent activities against wild-type (WT) HIV-1 with EC<sub>50</sub>
values ranging from 1.5 to 0.0064 μM. Among them, 5q was regarded as the most excellent compound against WT HIV-1 (EC<sub>50</sub>
= 6.4 nM, SI = 2500). And also, it displayed potent activities against K103 N (EC<sub>50</sub>
= 0.077 μM), Y181C (EC<sub>50</sub>
= 0.11 μM), E138K (EC<sub>50</sub>
= 0.057 μM), and moderate activity against double mutants RES056 (EC<sub>50</sub>
= 8.7 μM). Moreover, the structure-activity relationships (SARs) were summarized, and the molecular docking was performed to investigate the binding mode of IPAPYs and HIV-1 reverse transcriptase.</AbstractText>
<CopyrightInformation>Copyright © 2019 Elsevier Masson SAS. All rights reserved.</CopyrightInformation>
</Abstract>
<AuthorList CompleteYN="Y"><Author ValidYN="Y"><LastName>Xiao</LastName>
<ForeName>Ting</ForeName>
<Initials>T</Initials>
<AffiliationInfo><Affiliation>Key Laboratory for Green Chemical Process of Ministry of Education, School of Chemical Engineering & Pharmacy, Wuhan Institute of Technology, Wuhan, 430205, China.</Affiliation>
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<Author ValidYN="Y"><LastName>Tang</LastName>
<ForeName>Jia-Fan</ForeName>
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<AffiliationInfo><Affiliation>Key Laboratory for Green Chemical Process of Ministry of Education, School of Chemical Engineering & Pharmacy, Wuhan Institute of Technology, Wuhan, 430205, China.</Affiliation>
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<Keyword MajorTopicYN="N">Diaryl ethers</Keyword>
<Keyword MajorTopicYN="N">Indazole analogues</Keyword>
<Keyword MajorTopicYN="N">Molecular hybridization</Keyword>
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<Keyword MajorTopicYN="N">Piperidin-4-yl-aminopyrimidines</Keyword>
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<Month>11</Month>
<Day>06</Day>
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<Month>11</Month>
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