TY - JOUR
T1 - Synthesis of N-benzoyl Amino Esters and N-benzoyl Amino Acids and their Antifungal Activity
AU - Chiguils-Pérez, Yureli
AU - Rodríguez-Hurtado, Alejandro Israel
AU - Pérez-Picaso, Lemuel
AU - Martínez-Pascual, Roxana
AU - Martínez-Rivera, María de los Ángeles
AU - Hernández-Núñez, Emanuel
AU - Viñas-Bravo, Omar
AU - Rosete-Luna, Sharon
AU - Martínez-Galero, Nelda Xanath
N1 - Publisher Copyright:
©2022, Sociedad Química de México.
PY - 2022/12/31
Y1 - 2022/12/31
N2 - 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 Cα 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 α-carbon have been analyzed.
AB - 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 Cα 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 α-carbon have been analyzed.
KW - A. fumigatus
KW - Antifungal activity
KW - F. temperatum
KW - N-benzoyl amino acids
KW - N-benzoyl amino esters
UR - http://www.scopus.com/inward/record.url?scp=85123160105&partnerID=8YFLogxK
U2 - 10.29356/jmcs.v66i1.1584
DO - 10.29356/jmcs.v66i1.1584
M3 - Artículo
AN - SCOPUS:85123160105
SN - 1870-249X
VL - 66
SP - 95
EP - 107
JO - Journal of the Mexican Chemical Society
JF - Journal of the Mexican Chemical Society
IS - 1
ER -