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

• Authors: Daniel Cvejn , Věra Klimešová , Filip Bureš
• Languages of publication: EN

Abstracts

EN

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

EN

Imidazole; α-Amino acid; Antimycobacterial agents; SAR

• Publisher: De Gruyter Open
• Journal: Open Chemistry
• Year: 2012
• Volume: 10
• Issue: 5
• Pages: 1681-1687

Dates

published

1 - 10 - 2012

online

21 - 7 - 2012

Contributors

author

Daniel Cvejn

• Institute of Organic Chemistry and Technology, Faculty of Chemical Technology, University of Pardubice, CZ-53210, Pardubice, Czech Republic

author

Věra Klimešová

• Department of Inorganic and Organic Chemistry, Faculty of Pharmacy in Hradec Králové, Charles University in Prague, CZ-50005, Hradec Králové, Czech Republic

author

Filip Bureš

• Institute of Organic Chemistry and Technology, Faculty of Chemical Technology, University of Pardubice, CZ-53210, Pardubice, Czech Republic

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Identifiers

DOI

10.2478/s11532-012-0087-1