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α-Amino acid-derived 2-phenylimidazoles with potential antimycobacterial activity

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Central European Journal of Chemistry


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.

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Correspondence to Filip Bureš.

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Cvejn, D., Klimešová, V. & Bureš, F. α-Amino acid-derived 2-phenylimidazoles with potential antimycobacterial activity. cent.eur.j.chem. 10, 1681–1687 (2012).

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