[Ribonucleoside and 2'-deoxyribonucleoside 5'-phosphonates: synthesis and antiviral activity]

Mol Biol (Mosk). 1994 Jan-Feb;28(1):224-32.
[Article in Russian]

Abstract

Groups of 5'-phosphonates of natural 2'-deoxynucleosides and ribonucleosides were synthesized by condensation of 3'-acetylated 2'-deoxynucleosides or 2',3'-substituted (2',3'-O-isopropylidene, 2',3'-O-methoxymethylene, or 2',3'-O-ethoxymethylene) ribonucleosides. As condensing agents, either N,N'-dicyclohexylcarbodiimide or 2,4,6-triisopropylbenzenesulphonyl chloride were used. Nucleoside 5'-ethoxycarbonyl-phosphonates were converted into corresponding nucleoside 5'-aminocarbonylphosphonates by the action of ammonia in methanol. All compounds were tested for inhibition of several viruses, including human herpes simplex virus type 2 and cytomegalovirus, but showed no activity. A few compounds insignificantly inhibited human immunodeficiency virus type 1 reproduction. Thymidine 5'-hydrogenphosphonate neutralized the anti HIV action of 3'-azido-3'-deoxythymidine, thus indirectly showing that it could be partly hydrolyzed in cell culture to corresponding thymidine.

Publication types

  • English Abstract

MeSH terms

  • Antiviral Agents / chemical synthesis*
  • Antiviral Agents / pharmacology*
  • Cells, Cultured
  • Cytomegalovirus / drug effects
  • Cytomegalovirus / physiology
  • Deoxyribonucleosides / chemistry*
  • Deoxyribonucleosides / pharmacology
  • HIV-1 / drug effects
  • HIV-1 / physiology
  • Organophosphorus Compounds / chemistry*
  • Ribonucleosides / chemistry*
  • Ribonucleosides / pharmacology
  • Simplexvirus / drug effects
  • Simplexvirus / physiology
  • Virus Replication / drug effects

Substances

  • Antiviral Agents
  • Deoxyribonucleosides
  • Organophosphorus Compounds
  • Ribonucleosides