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Journal of the Mexican Chemical Society

versión impresa ISSN 1870-249X


CHIGUILS-PEREZ, Yureli et al. Synthesis of N-benzoyl Amino Esters and N-benzoyl Amino Acids and their Antifungal Activity. J. Mex. Chem. Soc [online]. 2022, vol.66, n.1, pp.95-107.  Epub 05-Dic-2022. ISSN 1870-249X.

A series of N-benzoyl amino esters and N-benzoyl amino acids were synthesized from commercially available amino acids (Val, Ile, Leu, Ala, Phe, Trp) and were evaluated for their antifungal activity against two filamentous fungi, A. fumigatus and F. temperatum. According to the in vitro assays, five compounds (5-7, 10, 13) exhibited relevant antifungal activity against F. temperatum and two compounds (5 and 7) showed remarkable activity against both fungi strains. Some structure-activity relationships were established regarding the side chain at C( and the type of substituents on the aromatic ring in the benzoyl moiety. Docking calculations were performed in order to predict binding affinities between compounds prepared herein and fungal chitinase, a potential target against fungi; interactions involving the aromatic rings, the influence on the number of methyl substituents, and configurations on the (-carbon have been analyzed.

Palabras llave : N-benzoyl amino esters; N-benzoyl amino acids; antifungal activity; A. fumigatus; F. temperatum.

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