Abstract
A series of hitherto unknown 3'-α-[1,2,3]-substituted triazolo-2',3'-dideoxypyrimidine nucleoside analogues of the anti-HIV 3'-azido-3'-deoxythymidine (AZT) were synthesized through catalyzed alkyne-azide 1,3-dipolar cycloaddition (Huisgen reaction). Those 3'-[1,2,3]-triazolo analogues bearing an azido alkyl chain were evaluated for their anti-HIV activity against HIV-1 in primary human lymphocytes as well as for their cytotoxicity in different cells. None of them inhibit HIV replication (EC(50) > 20 μM); two of them were converted to their triphosphate form to evaluate their HIV-RT inhibition.
Publication types
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Research Support, N.I.H., Extramural
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Research Support, U.S. Gov't, Non-P.H.S.
MeSH terms
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Animals
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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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Anti-HIV Agents / toxicity
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Azides / chemistry
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Cell Line
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HIV Reverse Transcriptase / antagonists & inhibitors
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HIV-1 / drug effects*
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HIV-1 / enzymology
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Humans
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Nucleosides / chemical synthesis*
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Nucleosides / chemistry
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Nucleosides / pharmacology*
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Nucleosides / toxicity
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Structure-Activity Relationship
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Triazoles / chemistry*
Substances
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Anti-HIV Agents
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Azides
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Nucleosides
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Triazoles
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reverse transcriptase, Human immunodeficiency virus 1
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HIV Reverse Transcriptase