Synthesis and in vitro antimicrobial activity of new 2-[p-substituted-benzyl]-5-[substituted-carbonylamino]benzoxazoles

Tekiner-Gulbas B., ARPACI Ö., YILDIZ İ., Altanlar N.

EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, vol.42, no.10, pp.1293-1299, 2007 (SCI-Expanded) identifier identifier identifier

  • Publication Type: Article / Article
  • Volume: 42 Issue: 10
  • Publication Date: 2007
  • Doi Number: 10.1016/j.ejmech.2007.01.022
  • Journal Name: EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus, Index Chemicus (IC)
  • Page Numbers: pp.1293-1299
  • Keywords: 2-benzylbenzoxazole, antibacterial and antifungal activity, MICROBIOLOGICAL ACTIVITY, 2,5-DISUBSTITUTED BENZOXAZOLES, ACTINOMYCETE FRANKIA, MOLECULAR-STRUCTURE, BIOLOGICAL-ACTIVITY, CALCIMYCIN A-23187, DERIVATIVES, BENZIMIDAZOLES, AGENTS, BENZOTHIAZOLES
  • Ankara University Affiliated: Yes

Abstract

Some new 2-(benzyl/p-chlorobenzyl)-5-[(substituted-thienyl/pheny/phenylthiomethyl/benzyl)carbonylamino]benzoxazole derivatives have been synthesized by reacting 5-amino-2-(benzyl/p-chlorobenzyl)benzoxazoles with appropriate carboxylic acid chlorides. The structures of the synthesized compounds were confirmed by IR, H-1 NMR and MASS spectral data. In vitro antimicrobial activities of the compounds were investigated using twofold serial dilution technique against different two Gram-positive, two Gram-negative bacteria and three Candida spp. in comparison with standard drugs. Microbiological results indicated that the newly synthesized 2-(benzyl/p-chlorobenzyl)-5[(substituted-thienyl/phenyl/phenylthiomethyl/benzyl)carbonyl amino] benzoxazole derivatives (3-12) possessed a broad spectrum of activity having MIC values of 6.25-100 mu g/ml against the tested microorganisms. Especially, with an MIC value of 6.25 mu g/ml, 2-(p-chlorophenyl)-5-[(2,5-dimethylphenyl)carbonylamino]benzoxazole 4 displayed the same activity against Candida albicans as the standard drug clotrimazole. (c) 2007 Elsevier Masson SAS. All rights reserved.