Synthesis, conformation, and antiviral activity of 5-methoxymethyl-2'-deoxycytidine analogs

Nucleosides Nucleotides Nucleic Acids. 2003 Feb;22(2):223-38. doi: 10.1081/NCN-120019532.

Abstract

Analogs of 5-methoxymethyl-2'-deoxycytidine, MMdCyd (1) by substitution at N4 were synthesized to impart resistance against deamination. The anti HSV-1 activity and solution conformation of analogs were determined. N4-Butanoyl-MMdCyd (10) was a potent inhibitor of HSV-1 replication while N4-hexanoyl-MMdCyd (11), N4-propanoyl-MMdCyd (9) and N4-acetyl-MMdCyd (8) had good activity against HSV-1 replication. All other analogs were devoid of activity against HSV-1.

Publication types

  • Comparative Study
  • Research Support, Non-U.S. Gov't

MeSH terms

  • Antiviral Agents / chemical synthesis
  • Antiviral Agents / pharmacology
  • Antiviral Agents / toxicity
  • Chromatography, High Pressure Liquid
  • Crystallography, X-Ray
  • Deamination / drug effects
  • Deoxycytidine / analogs & derivatives*
  • Deoxycytidine / chemical synthesis*
  • Deoxycytidine / pharmacology
  • Drug Stability
  • Herpesvirus 1, Human / drug effects
  • Magnetic Resonance Spectroscopy
  • Molecular Conformation
  • Molecular Structure

Substances

  • Antiviral Agents
  • Deoxycytidine
  • 5-methoxymethyl-2-deoxycytidine