Synthesis and antimicrobial activities of hexahydroimidazo[1,5-a]pyridinium bromides with varying benzyl substituents

Turkmen H. , Ceyhan N., Yavasoglu N. U. K. , Ozdemir G. , Cetinkaya B.

EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, cilt.46, ss.2895-2900, 2011 (SCI İndekslerine Giren Dergi) identifier identifier identifier

  • Cilt numarası: 46 Konu: 7
  • Basım Tarihi: 2011
  • Doi Numarası: 10.1016/j.ejmech.2011.04.012
  • Sayfa Sayıları: ss.2895-2900


Variously substituted benzyl bromides were employed to quaternize hexahydrobenzylimidazo[1,5-a] pyridine (A) and the resulting bromides (1-11) were evaluated for their in vitro antimicrobial activity against 10 pathogenic microorganisms: Staphylococcus aureus, Staphylococcus epidermidis, Bacillus cereus, Micrococcus luteus, Proteus vulgaris, Escherichia coli, Salmonella typhimurium, Klebsiella pneumonia, Candida albicans and Candida krusei. Antimicrobial activities were surprisingly high (MIC: 0.78-400 mu g/mL) and the sensitivity of the salts tested has been found to depend strongly both on the benzyl substituents and the microorganisms used. However, the correlation observed between antimicrobial activity and calculated partition coefficient (ClogP) was poor. Acute toxicity assessment of these salts showed LD(50) of 757-2000 mg/kg, after oral administration in mice in 24 h. (C) 2011 Elsevier Masson SAS. All rights reserved.