Synthesis and biological evaluation of 6-amino-1H-pyrrolo[3,2-c]pyridin-4(5H)-one (3,7-dideazaguanine)

J Med Chem. 1984 Dec;27(12):1737-9. doi: 10.1021/jm00378a037.

Abstract

The synthesis of 6-amino-1H-pyrrolo[3,2-c]pyridin-4(5H)-one (3,7-dideazaguanine, 2) has been accomplished from 3-(ethoxycarbonyl)pyrrole-2-acetonitrile. In contrast to 3-deazaguanine, compound 2 did not show any antitumor, antiviral, or antibacterial properties. Furthermore, it was not a substrate for hypoxanthine-guanine phosphoribosyltransferase or purine nucleoside phosphorylase.

Publication types

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

MeSH terms

  • Animals
  • Anti-Bacterial Agents
  • Anti-Infective Agents / chemical synthesis*
  • Cell Division / drug effects
  • Cell Line
  • Cricetinae
  • Cricetulus
  • Erythrocytes / enzymology
  • Escherichia coli / drug effects
  • Female
  • Guanine / analogs & derivatives*
  • Guanine / chemical synthesis
  • Guanine / pharmacology
  • Guanine / toxicity
  • Humans
  • Hypoxanthine Phosphoribosyltransferase / blood
  • Indicators and Reagents
  • Microbial Sensitivity Tests
  • Ovary
  • Purine-Nucleoside Phosphorylase / blood
  • Structure-Activity Relationship
  • Viruses / drug effects

Substances

  • Anti-Bacterial Agents
  • Anti-Infective Agents
  • Indicators and Reagents
  • Guanine
  • 3,7-dideazaguanine
  • Purine-Nucleoside Phosphorylase
  • Hypoxanthine Phosphoribosyltransferase