title: Synthesis and antimicrobial activities of hexahydroimidazo[1,5-a]pyridinium bromides with varying benzyl substituents.
abstract: 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 μg/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 24h.
authors.affiliation: Ege University, Department of Chemistry, 35100 Bornova-Izmir, Turkey. hayatiturkmen@hotmail.com
authors.forename: Hayati
authors.initials: H
authors.lastname: Türkmen
authors.forename: Nur
authors.initials: N
authors.lastname: Ceyhan
authors.forename: N
authors.initials: N
authors.lastname: Ulkü Karabay Yavaşoğlu
authors.forename: Güven
authors.initials: G
authors.lastname: Ozdemir
authors.forename: Bekir
authors.initials: B
authors.lastname: Cetinkaya
mesh_terms: D000900:Anti-Bacterial Agents / Q000138:chemical synthesis* / Q000494:pharmacology; D000935:Antifungal Agents / Q000138:chemical synthesis* / Q000494:pharmacology; D001965:Bromides / Q000737:chemistry*; D002175:Candida / Q000187:drug effects / Q000254:growth & development; D004755:Enterobacteriaceae / Q000187:drug effects / Q000254:growth & development; D007093:Imidazoles / Q000737:chemistry*; D008826:Microbial Sensitivity Tests; D016982:Micrococcus luteus / Q000187:drug effects / Q000254:growth & development; D011726:Pyridinium Compounds / Q000138:chemical synthesis* / Q000494:pharmacology; D013210:Staphylococcus / Q000187:drug effects / Q000254:growth & development; D013329:Structure-Activity Relationship
chemical_list: D000900:Anti-Bacterial Agents; D000935:Antifungal Agents; D001965:Bromides; D007093:Imidazoles; D011726:Pyridinium Compounds