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a-Amino acid-derived 2-phenylimidazoles with potential antimycobacterial activity
Authors: Cvejn Daniel | Klimešová Věra | Bureš Filip
Year: 2012
Type of publication: článek v odborném periodiku
Name of source: Central European Journal of Chemistry
Publisher name: Springer
Page from-to: 1681-1687
Titles:
Language Name Abstract Keywords
cze Deriváty 2-fenylimidazolu s motivem a-aminokyselin s potenciální antimykobakteriální aktivitou Byly navrženy a syntetizovány deriváty 2-fenylimidazolu s motivem a-aminokyselin s potenciální antimykobakteriální aktivitou. Syntéza zahrnovala transformaci Cbz-chráněných a-aminokyselin na diazoketony a bromokoetony a jejich následnou kondenzaci se (4-nitro)benzamidinem. Vzniklé deriváty 2-fenylimidazolu nesou a-aminokyselinouvý zbytek v poloze C4 imidazolu. Antimykobakteriální aktivity byly studovány proti kmenům M. tuberculosis, M. avium a M. kansasii a následně byly vyvozeny základní vztahy struktura-vlastnosti. imidazol; antimykobakteriální látka; a-aminokyselina; syntéza
eng a-Amino acid-derived 2-phenylimidazoles with potential antimycobacterial activity α-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 α-amino acids (Ala, Val, Phe, Leu, iLe, and Pro) into α-diazoketones and α-bromoketones, respectively. Subsequent treatment of α-bromoketones with (4-nitro) benzamidine afforded imidazole derivatives bearing α-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. imidazole; antimycobacterial agent; a-amino acid; synthesis

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