Abstract
With the help of Surflex-Dock calculation, two ritonavir analogs in which one thioazole unit was replaced by selenazole have been designed and synthesized. The key selenazole structure was constructed from β-azido diselenide through a cascade diselenide cleavage/selenocarbonylation/Staudinger reduction/aza-Wittig reaction and a following MnO2 oxidation. The accordingly prepared compounds exhibited good anti-HIV-1 (IIIB) activities comparable to that of the original ritonavir, as well as the positive SI values.
Keywords:
Antiviral; One-pot reaction; Protease inhibitor; Ritonavir; Selenazole.
Copyright © 2018 Elsevier Ltd. All rights reserved.
Publication types
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Research Support, Non-U.S. Gov't
MeSH terms
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Anti-HIV Agents / chemical synthesis
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Anti-HIV Agents / chemistry
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Anti-HIV Agents / pharmacology*
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Azoles / chemistry
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Azoles / pharmacology*
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Dose-Response Relationship, Drug
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Drug Design
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HIV / drug effects*
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HIV Protease Inhibitors / chemical synthesis
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HIV Protease Inhibitors / chemistry
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HIV Protease Inhibitors / pharmacology*
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Manganese Compounds / chemistry
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Microbial Sensitivity Tests
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Models, Molecular
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Molecular Structure
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Organoselenium Compounds / chemistry
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Organoselenium Compounds / pharmacology*
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Oxidation-Reduction
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Oxides / chemistry
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Ritonavir / chemical synthesis
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Ritonavir / chemistry
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Ritonavir / pharmacology*
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Structure-Activity Relationship
Substances
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Anti-HIV Agents
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Azoles
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HIV Protease Inhibitors
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Manganese Compounds
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Organoselenium Compounds
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Oxides
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manganese oxide
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Ritonavir