Synthesis and biological activity of the diphosphorylphosphonate derivatives of (+)- and (–)-cis-9-(4′-hydroxycyclopent-2′-enyl)guanine
- 1 January 1994
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 1
- No. 11,p. 1477-1481
- https://doi.org/10.1039/p19940001477
Abstract
The carbovir triphosphate analogue 10 and its enantiomer 11 have been synthesized and tested as inhibitors of HIV-reverse transcriptase; the enantiomer 11, more remotely resembling natural nucleotides in stereochemical terms, is surprisingly the more active compound.This publication has 13 references indexed in Scilit:
- The Resolution and Absolute Stereochemistry of the Enantiomers ofcis-1-[2-(Hydroxymethyl)-1,3-oxathiolan-5-yl)cytosine (BCH189): Equipotent Anti-HIV AgentsNucleosides and Nucleotides, 1993
- Oxidative degradation of L-ascorbic acid acetals to 2′,3′-dideoxy-3′-oxaribofuranosides. Synthesis of enantiomerically pure 2′,3′-dideoxy-3′-oxacytidine stereoisomers as potential antiviral agentsTetrahedron Letters, 1992
- Potent anti-HIV and anti-HBV activities of (−)-L-β-dioxolane-C and (+)-L-β-dioxolane-T and their asymmetric syntheses.Tetrahedron Letters, 1992
- Effects of (-)-2'-deoxy-3'-thiacytidine (3TC) 5'-triphosphate on human immunodeficiency virus reverse transcriptase and mammalian DNA polymerases alpha, beta, and gammaAntimicrobial Agents and Chemotherapy, 1992
- The potential of carbocyclic nucleosides for the treatment of AIDS: synthesis of some diphosphorylphosphonates possessing potent activity against HIV-coded reverse transcriptaseJournal of the Chemical Society, Perkin Transactions 1, 1992
- Preparation of the geometric isomers of DDC, DDA, D4C and D4T as potential anti-HIV agentsBioorganic & Medicinal Chemistry Letters, 1991
- Synthesis of L-3'-azido-3'-deoxythymidine (L-AZT) and its stereoisomersThe Journal of Organic Chemistry, 1991
- Synthesis and antiviral activity of the enantiomeric forms of carba-5-iodo-2'-deoxyuridine and carba-(E)-5-(2-bromovinyl)-2'-deoxyuridineJournal of Medicinal Chemistry, 1989
- Preparation of 5'-O-phosphonylmethyl analogues of nucleoside-5'-phosphates, 5'-diphosphates and 5'-triphosphatesCollection of Czechoslovak Chemical Communications, 1982
- Rapid chromatographic technique for preparative separations with moderate resolutionThe Journal of Organic Chemistry, 1978