Salicylanilide esters of N-protected amino acids as novel antimicrobial agents.
A series of novel, highly antimicrobial salicylanilide esters of N-protected amino acids were synthesized and characterized. Their in vitro antimicrobial activity against eight fungal strains and Mycobacterium tuberculosis was determined. The compounds had the highest level of activity against Aspergillus fumigatus, Absidia corymbifera and Trichophyton mentagrophytes, and these levels were higher than that of the standard drug fluconazole. In addition, three compounds showed interesting antituberculosis activity, with inhibition ranging from 89% to 99%. (S)-4-Chloro-2-(4-trifluoromethylphenylcarbamoyl)-phenyl 2-benzyloxy-carbonylamino-propionate had the highest level of both antifungal and antimycobacterial activity. The structure-activity relationships of the new compounds are discussed.
Imramovský
Ales
A
Department of Inorganic and Organic Chemistry, Faculty of Pharmacy, Charles University, Heyrovskeho 1203, 500 05 Hradec Kralove, Czech Republic. ales.imramovsky@faf.cuni.cz
Vinsová
Jarmila
J
Férriz
Juana Monreal
JM
Buchta
Vladimír
V
Jampílek
Josef
J
D020095:Absidia / Q000187:drug effects; D000596:Amino Acids / Q000737:chemistry*; D000890:Anti-Infective Agents / Q000737:chemistry / Q000494:pharmacology*; D001232:Aspergillus fumigatus / Q000187:drug effects; D004952:Esters; D008826:Microbial Sensitivity Tests; D009169:Mycobacterium tuberculosis / Q000187:drug effects; D012458:Salicylanilides / Q000737:chemistry / Q000494:pharmacology*; D014249:Trichophyton / Q000187:drug effects
D000596:Amino Acids; D000890:Anti-Infective Agents; D004952:Esters; D012458:Salicylanilides; C034596:salicylanilide