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Synthesis and evaluation of 2'-substituted cyclobutyl nucleosides and nucleotides as potential anti-HIV agents. 2007
Yongfeng Li, and
Shuli Mao, and
Michael W Hager, and
Kimberlynne D Becnel, and
Raymond F Schinazi, and
Dennis C Liotta
Department of Chemistry, Emory University, Atlanta, GA 30322, USA.
A series of 2'-substituted cyclobutyl nucleoside analogs were efficiently prepared by constructing the core cyclobutyl ring using different [2+2] cycloaddition approaches. The triphosphate derivative of a cyclobutyl nucleoside was also synthesized and evaluated against wild-type and mutant HIV reverse transcriptases (RT). Whereas the nucleoside analogs were inactive against HIV-1 in culture, the nucleotide showed good activity not only against wild-type and recombinant HIV RT (IC(50)=4.7, 6.9 microM), but also against the M184I and M184V mutants (IC(50)=6.1, 6.9 microM) in cell-free assays.
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