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• W2035698568 abstract "The triphosphates of antiviral 2',3'-dideoxynucleosides (ddNs) are the active chemical species that inhibit viral DNA synthesis. The inhibition involves incorporation of ddNMP into DNA and subsequent chain termination. A conceivable strategy for antiviral drugs is to employ nucleoside 5'-triphosphate mimics that can entirely bypass cellular phosphorylation. AZT 5'-alpha-R(P)-borano-beta,gamma-(difluoromethylene)triphosphate (5'-alphaB-betagammaCF(2)TP) has been identified as a potent inhibitor of HIV-1 reverse transcriptase (HIV-1 RT). This work was aimed at confirming that 5'-alphaB-betagammaCF(2)TP is a useful generic triphosphate moiety and can render antiviral ddNs with potent inhibitory effects on HIV-1 RT. Thus, 10 ddNs were converted to their 5'-alphaB-betagammaCF(2)TPs via a sequence (one-pot) of reactions: formation of an activated phosphite, formation of a cyclic triphosphate, boronation, and hydrolysis. Other synthetic routes were also explored. All ddN 5'-alphaB-betagammaCF(2)TPs tested exhibited essentially the same level of inhibition of HIV-1 RT as the corresponding ddNTPs. A conclusion can be made that 5'-alphaB-betagammaCF(2)TP is a generic and promising triphosphate mimic (P3M) concerning HIV-1 RT inhibition and serum stability. It is anticipated that use of 5'-alphaB-betagammaCF(2)TP as P3M moiety will lead to the discovery of a new class of anti-HIV agents." @default.
• W2035698568 created "2016-06-24" @default.
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• W2035698568 date "2005-02-25" @default.
• W2035698568 modified "2023-09-30" @default.
• W2035698568 title "Synthesis of 2‘,3‘-Dideoxynucleoside 5‘-α-<i>P</i>-Borano-β,γ-(difluoromethylene)triphosphates and Their Inhibition of HIV-1 Reverse Transcriptase" @default.
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• W2035698568 doi "https://doi.org/10.1021/jm040101y" @default.
• W2035698568 hasPubMedId "https://pubmed.ncbi.nlm.nih.gov/15801860" @default.
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