Abstract
The bis(tributylstannyl) derivative of 2',3'-didehydro-2',3'-dideoxyuridine (d4U) underwent an anionic 5'-O-->3'-C stannyl migration to yield the 3'-tributylstannyl-d4U. This compound, with its vinylstannane structure, allowed ready access to the preparation of 3'-carbon-substituted analogues through the Stille reaction. A conventional transformation of the uracil moiety of these d4U analogues led to the corresponding 2',3'-didehydro-2',3'-dideoxycytidine (d4C) counterparts. Some 2',3'-dideoxycytidine (ddC) analogues were also synthesized. Antiviral evaluation revealed that none of these analogues showed activity against HIV, hepatitis B virus, herpes simplex virus-1 (HSV-1) and HSV-2.
Publication types
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Research Support, Non-U.S. Gov't
MeSH terms
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Animals
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Anti-HIV Agents / chemical synthesis
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Anti-HIV Agents / pharmacology*
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Antiviral Agents / chemical synthesis*
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Antiviral Agents / pharmacology
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Cells, Cultured
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Chlorocebus aethiops
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Dideoxynucleosides / chemical synthesis*
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Drug Evaluation, Preclinical
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HIV-1 / drug effects
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Hepatitis B virus / drug effects
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Humans
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Models, Biological
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Pyrimidine Nucleosides / chemical synthesis*
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Pyrimidine Nucleosides / chemistry*
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Simplexvirus / drug effects
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Vero Cells
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Zalcitabine / chemical synthesis*
Substances
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Anti-HIV Agents
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Antiviral Agents
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Dideoxynucleosides
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Pyrimidine Nucleosides
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2',3'-didehydro-2',3'-dideoxyuridine
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Zalcitabine