5′-Silylated 3′-1,2,3-triazolyl Thymidine Analogues as Inhibitors of West Nile Virus and Dengue Virus
Identifieur interne : 002A66 ( Ncbi/Checkpoint ); précédent : 002A65; suivant : 002A675′-Silylated 3′-1,2,3-triazolyl Thymidine Analogues as Inhibitors of West Nile Virus and Dengue Virus
Auteurs : Sanjeev Kumar V. Vernekar [États-Unis] ; Li Qiu [États-Unis] ; Jing Zhang [États-Unis] ; Jayakanth Kankanala [États-Unis] ; Hongmin Li [États-Unis] ; Robert J. Geraghty [États-Unis] ; Zhengqiang Wang [États-Unis]Source :
- Journal of medicinal chemistry [ 0022-2623 ] ; 2015.
Descripteurs français
- KwdFr :
- Adémétionine (), Antiviraux (), Antiviraux (pharmacologie), Fixation compétitive, Methyltransferases (), Relation dose-effet des médicaments, Relation structure-activité, Silanes (), Silanes (pharmacologie), Simulation de docking moléculaire, Stéréoisomérie, Triazoles (), Triazoles (pharmacologie), VIH-1 (Virus de l'Immunodéficience Humaine de type 1) (), Virus de la dengue (), Virus du Nil occidental (), Zidovudine (), Zidovudine (analogues et dérivés), Zidovudine (pharmacologie).
- MESH :
- analogues et dérivés : Zidovudine.
- pharmacologie : Antiviraux, Silanes, Triazoles, Zidovudine.
- Adémétionine, Antiviraux, Fixation compétitive, Methyltransferases, Relation dose-effet des médicaments, Relation structure-activité, Silanes, Simulation de docking moléculaire, Stéréoisomérie, Triazoles, VIH-1 (Virus de l'Immunodéficience Humaine de type 1), Virus de la dengue, Virus du Nil occidental, Zidovudine.
English descriptors
- KwdEn :
- Antiviral Agents (chemistry), Antiviral Agents (pharmacology), Binding, Competitive, Dengue Virus (drug effects), Dose-Response Relationship, Drug, HIV-1 (drug effects), Methyltransferases (chemistry), Molecular Docking Simulation, S-Adenosylmethionine (chemistry), Silanes (chemistry), Silanes (pharmacology), Stereoisomerism, Structure-Activity Relationship, Triazoles (chemistry), Triazoles (pharmacology), West Nile virus (drug effects), Zidovudine (analogs & derivatives), Zidovudine (chemistry), Zidovudine (pharmacology).
- MESH :
- chemical , analogs & derivatives : Zidovudine.
- chemical , chemistry : Antiviral Agents, Methyltransferases, S-Adenosylmethionine, Silanes, Triazoles, Zidovudine.
- chemical , pharmacology : Antiviral Agents, Silanes, Triazoles, Zidovudine.
- drug effects : Dengue Virus, HIV-1, West Nile virus.
- Binding, Competitive, Dose-Response Relationship, Drug, Molecular Docking Simulation, Stereoisomerism, Structure-Activity Relationship.
Abstract
West Nile virus (WNV) and Dengue virus (DENV) are important human pathogens for which there are presently no vaccine or specific antivirals. We report herein a 5′-silylated nucleoside scaffold derived from 3′-azidothymidine (AZT) consistently and selectively inhibiting WNV and DENV at low micromolar concentrations. Further synthesis of various triazole bioisosteres demonstrated clear structure–activity relationships (SARs) in which the antiviral activity against WNV and DENV hinges largely on both the 5′-silyl group and the substituent of 3′-triazole or its bioisosteres. Particularly interesting is the 5′ silyl group which turns on the antiviral activity against WNV and DENV while abrogating the previously reported antiviral potency against human immunodeficiency virus (HIV-1). The antiviral activity was confirmed through a plaque assay where viral titer reduction was observed in the presence of selected compounds. Molecular modeling and competitive
Url:
DOI: 10.1021/acs.jmedchem.5b00327
PubMed: 25909386
PubMed Central: 4465584
Affiliations:
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<profileDesc><textClass><keywords scheme="KwdEn" xml:lang="en"><term>Antiviral Agents (chemistry)</term>
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<term>Binding, Competitive</term>
<term>Dengue Virus (drug effects)</term>
<term>Dose-Response Relationship, Drug</term>
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<term>Methyltransferases (chemistry)</term>
<term>Molecular Docking Simulation</term>
<term>S-Adenosylmethionine (chemistry)</term>
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<term>Stereoisomerism</term>
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<term>Triazoles (pharmacology)</term>
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<front><div type="abstract" xml:lang="en"><p id="P1">West Nile virus (WNV) and Dengue virus (DENV) are important human pathogens for which there are presently no vaccine or specific antivirals. We report herein a 5′-silylated nucleoside scaffold derived from 3′-azidothymidine (AZT) consistently and selectively inhibiting WNV and DENV at low micromolar concentrations. Further synthesis of various triazole bioisosteres demonstrated clear structure–activity relationships (SARs) in which the antiviral activity against WNV and DENV hinges largely on both the 5′-silyl group and the substituent of 3′-triazole or its bioisosteres. Particularly interesting is the 5′ silyl group which turns on the antiviral activity against WNV and DENV while abrogating the previously reported antiviral potency against human immunodeficiency virus (HIV-1). The antiviral activity was confirmed through a plaque assay where viral titer reduction was observed in the presence of selected compounds. Molecular modeling and competitive <italic>S</italic>
-adenosyl-L-methionine (SAM) binding assay suggest that these compounds likely confer antiviral activity via binding to methyltransferase (MTase).</p>
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