Publication at Faculty of Pharmacy in Hradec Králové |
2012
Abstract
alpha-Amino acid-derived 2-phenylimidazole derivatives were designed, synthesized, and further investigated as potential antimycobacterial agents. The synthesis of target imidazole derivatives involved the transformation of Cbz-protected alpha-amino acids (Ala, Val, Phe, Leu, iLe, and Pro) into alpha-diazoketones and alpha-bromoketones, respectively.
Subsequent treatment of alpha-bromoketones with (4-nitro)benzamidine afforded imidazole derivatives bearing alpha-amino acid residue appended to the imidazole C4 and (4-nitro)phenyl ring in the position C2. Antimycobacterial activities of both series of compounds against M. tuberculosis, M. avium, and M. kansasii were screened and basic structure-activity relationships were further evaluated.