Synthesis and antimicrobial evaluation of some new substituted purine derivatives

Bioorg Med Chem. 2009 Feb 15;17(4):1693-700. doi: 10.1016/j.bmc.2008.12.050. Epub 2008 Dec 29.

Abstract

A series of 8,9-disubstituted adenines (4, 5, 8), 6-substituted aminopurines (10-13) and 9-(p-fluorobenzyl/cyclopentyl)-6-substituted aminopurines (16, 17, 19-30) have been prepared and the antimicrobial activities of these compounds against Staphylococcus aureus, methicillin-resistant S. aureus (MRSA, standard and clinical isolate), Bacillus subtilis, Escherichia coli and Candida albicans were evaluated. 6-[(N-phenylaminoethyl)amino]-9H-purine (12) which has no substitution at N-9 position and 9-cyclopentyl-6-[(4-fluorobenzyl)amino]-9H-purine (24) exhibited excellent activity against C. albicans with MIC 3.12 microg/mL. These compounds displayed better antifungal activity than that of standard oxiconazole. Furthermore, compound 22 carrying 4-chlorobenzylamino group at the 6-position of the purine moiety exhibited comparable antibacterial activity with that of the standard ciprofloxacin against both of the drug-resistant bacteria (MRSA, standard and clinical isolate).

MeSH terms

  • Anti-Infective Agents / chemical synthesis*
  • Anti-Infective Agents / chemistry
  • Anti-Infective Agents / pharmacology*
  • Methicillin Resistance / drug effects
  • Microbial Sensitivity Tests
  • Purines / chemical synthesis*
  • Purines / chemistry
  • Purines / pharmacology*
  • Staphylococcus aureus / drug effects
  • Structure-Activity Relationship

Substances

  • Anti-Infective Agents
  • Purines