Synthesis of New Nucleoside Analogues Comprising a Geminal Difluorocyclopropane Moiety as Potential Antiviral/Antitumor Agents
- 1 October 1999
- journal article
- research article
- Published by Taylor & Francis in Nucleosides and Nucleotides
- Vol. 18 (10) , 2285-2300
- https://doi.org/10.1080/07328319908044881
Abstract
Geminal difluorocyclopropane analogues of nucleosides 7a–7e were synthesized. Compounds 7a and 7c–7e were obtained by alkylation of nucleic acid bases or their appropriate precursors with (cis)-1-benzyloxymethyl-2-bromomethyl-3,3-difluorocyclopropane (8). Analogue 7b was prepared by hydrolysis of 2-amino-6-chloropurine derivative 7e. Compounds 7a–7d did not exhibit any antiviral activity against HCMV, HSV-1, HSV-2, EBV, VZV, HBV and HIV-1 or antitumor effects against murine leukemia L1210, mouse tumors PO3 or C38 and human tumor H15.Keywords
This publication has 19 references indexed in Scilit:
- Synthesis and Antiviral Activity of Novel Acyclic Nucleosides: Discovery of a Cyclopropyl Nucleoside with Potent Inhibitory Activity against HerpesvirusesJournal of Medicinal Chemistry, 1998
- (Z)- and (E)-2-((Hydroxymethyl)cyclopropylidene)methyladenine and -guanine. New Nucleoside Analogues with a Broad-Spectrum Antiviral ActivityJournal of Medicinal Chemistry, 1998
- Synthesis, Absolute Configuration, and Enantioselectivity of Antiretroviral Effect of (R)-(-)- and (S)-(+)-Cytallene. Lipase-Catalyzed Enantioselective Acylations of (.+-.)-N4-AcylcytallenesJournal of Medicinal Chemistry, 1995
- AIDS-driven nucleoside chemistry.Chemical Reviews, 1992
- Unsaturated and carbocyclic nucleoside analogs: synthesis, antitumor and antiviral activityJournal of Medicinal Chemistry, 1991
- Synthesis of Nucleosides Fluorinated in the Sugar Moiety. The Application of Diethylaminosulfur Trifluoride to the Synthesis of Fluorinated NucleosidesNucleosides and Nucleotides, 1989
- Synthesis and antiherpetic activity of (.+-.)-9-[[(Z)-2-(hydroxymethyl)cyclopropyl]methyl]guanine and related compoundsJournal of Medicinal Chemistry, 1988
- SYNTHETIC APPROACH TOWARD MITOMYCINS. SYNTHESIS OF 9-BENZYLOXYMETHYL-5-METHOXY-4-METHYL-3H-PYRROLO[1,2-a]INDOL-4,5-DIONEChemistry Letters, 1983
- Protection of hydroxyl groups as tert-butyldimethylsilyl derivativesJournal of the American Chemical Society, 1972
- Halo sugar nucleosides. III. Reactions for the chlorination and bromination of nucleoside hydroxyl groupsThe Journal of Organic Chemistry, 1972