Central European Journal of Chemistry

, Volume 10, Issue 5, pp 1681–1687 | Cite as

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

Research Article

Abstract

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.

Keywords

Imidazole α-Amino acid Antimycobacterial agents SAR 

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Copyright information

© Versita Warsaw and Springer-Verlag Wien 2012

Authors and Affiliations

  1. 1.Institute of Organic Chemistry and Technology, Faculty of Chemical TechnologyUniversity of PardubicePardubiceCzech Republic
  2. 2.Department of Inorganic and Organic Chemistry, Faculty of Pharmacy in Hradec KrálovéCharles University in PragueHradec KrálovéCzech Republic

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