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pubmed:abstractText |
This is the first report describing the synthesis and conformation of methanocarba nucleosides incorporating an endo (beta-face) cyclopropyl at the 2',3' position of 2',3'-didehydro-2',3'-dideoxy carbocyclic nucleosides. These nucleoside isosteres have been shown to exist in a unique extreme eastern conformation. This prediction was confirmed by x-ray crystallography and high resolution NMR spectroscopy. As expected, the methanocarba adenosine compound was neither a substrate nor an inhibitor of adenosine deaminase. However, some of the compounds synthesized demonstrated moderate antiviral activity against HSV-1. The methanocarba adenosine and its triphosphate form were evaluated as inhibitors of HIV-1 reverse transcriptase.
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pubmed:affiliation |
Department of Medicinal Chemistry, College of Pharmacy, University of Minnesota, 308 Harvard Street S. E., Minneapolis, MN 55455, USA.
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