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Open Chemistry

formerly Central European Journal of Chemistry

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Volume 10, Issue 5


Volume 13 (2015)

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

Daniel Cvejn
  • Institute of Organic Chemistry and Technology, Faculty of Chemical Technology, University of Pardubice, CZ-53210, Pardubice, Czech Republic
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/ Věra Klimešová
  • Department of Inorganic and Organic Chemistry, Faculty of Pharmacy in Hradec Králové, Charles University in Prague, CZ-50005, Hradec Králové, Czech Republic
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/ Filip Bureš
  • Institute of Organic Chemistry and Technology, Faculty of Chemical Technology, University of Pardubice, CZ-53210, Pardubice, Czech Republic
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Published Online: 2012-07-21 | DOI: https://doi.org/10.2478/s11532-012-0087-1


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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About the article

Published Online: 2012-07-21

Published in Print: 2012-10-01

Citation Information: Open Chemistry, Volume 10, Issue 5, Pages 1681–1687, ISSN (Online) 2391-5420, DOI: https://doi.org/10.2478/s11532-012-0087-1.

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© 2012 Versita Warsaw. This work is licensed under the Creative Commons Attribution-NonCommercial-NoDerivatives 3.0 License. BY-NC-ND 3.0

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