Synthesis and antimicrobial evaluation of some new substituted purine derivatives

Tuncbilek M., Ates-Alagoz Z., Altanlar N., KARAYEL A., ÖZBEY S.

BIOORGANIC & MEDICINAL CHEMISTRY, vol.17, no.4, pp.1693-1700, 2009 (SCI-Expanded) identifier identifier identifier

  • Publication Type: Article / Article
  • Volume: 17 Issue: 4
  • Publication Date: 2009
  • Doi Number: 10.1016/j.bmc.2008.12.050
  • Journal Name: BIOORGANIC & MEDICINAL CHEMISTRY
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Page Numbers: pp.1693-1700
  • Hacettepe University Affiliated: Yes

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 mu g/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). (C) 2008 Elsevier Ltd. All rights reserved.