Antimycobacterial agents. 1. Thio analogues of purine

J Med Chem. 2004 Jan 1;47(1):273-6. doi: 10.1021/jm030389b.

Abstract

Thio analogues of purine, pyridine, and pyrimidine were prepared based on the initial activity screening of several analogues of these heterocycles against Mycobacterium tuberculosis (Mtb). Certain 6-thio-substituted purine analogues described herein showed moderate to good inhibitory activity. In particular, two purine analogues 9-(ethylcarboxymethyl)-6-(decylthio)-9H-purine (20) and 9-(ethylcarboxymethyl)-6-(dodecylthio)-9H-purine (21) exhibited MIC values of 1.56 and 0.78 microg/mL respectively against the Mtb H(37)Rv strain. N(9)-Substitution apparently enhances the antimycobacterial activity in the purine series described herein.

Publication types

  • Research Support, U.S. Gov't, P.H.S.

MeSH terms

  • Antitubercular Agents / chemical synthesis*
  • Antitubercular Agents / chemistry
  • Antitubercular Agents / pharmacology
  • Microbial Sensitivity Tests
  • Mycobacterium tuberculosis / drug effects
  • Purines / chemical synthesis*
  • Purines / chemistry
  • Purines / pharmacology
  • Pyridines / chemical synthesis
  • Pyridines / chemistry
  • Pyridines / pharmacology
  • Pyrimidines / chemical synthesis
  • Pyrimidines / chemistry
  • Pyrimidines / pharmacology
  • Sulfides / chemical synthesis*
  • Sulfides / chemistry
  • Sulfides / pharmacology

Substances

  • 9-(ethylcarboxymethyl)-6-(decylthio)-9H-purine
  • 9-(ethylcarboxymethyl)-6-(dodecylthio)-9H-purine
  • Antitubercular Agents
  • Purines
  • Pyridines
  • Pyrimidines
  • Sulfides