TY - JOUR
T1 - Synthesis of alkoxy-isoflavones as potential α-glucosidase inhibitors
AU - Aguila-Muñoz, Dolores G.
AU - Cervantes-Espinoza, Elizabeth
AU - Escalante, Carlos H.
AU - Gutiérrez, Rsuini U.
AU - Cruz-López, María C.
AU - Jiménez-Montejo, Fabiola E.
AU - Villa-Ruano, Nemesio
AU - Gómez-García, Omar
AU - Tamariz, Joaquín
AU - Mendieta-Moctezuma, Aarón
N1 - Publisher Copyright:
© 2022, The Author(s), under exclusive licence to Springer Science+Business Media, LLC, part of Springer Nature.
PY - 2022/8
Y1 - 2022/8
N2 - The aim of the present study was to synthesize isoflavone-enaminones 3a-c and 7-alkoxy-isoflavones 4a-c, evaluate their inhibition of α-glucosidase, and analyze the bioisosteric effect of the presence versus absence of aromatic moieties in these benzopyran derivatives. All the test compounds exhibited greater inhibition of α-glucosidase than the positive control acarbose. The series of isoflavones 3a-c and 4a-c showed higher inhibitory activity (IC50 = 6.3–87.6 µM) than the parental 7-hydroxyisoflavones 2a-c (IC50 = 109.4–173.2 µM), suggesting that the attachment of a 4’-chloroacetophenone moiety to the 7-hydroxyl group of 2a-c is an efficient way to increase the inhibition of α-glucosidase. Furthermore, the aromatic moieties of the series of compounds 3 and 4 enhance inhibitory activity by hydrophobic effects, according to docking calculations. [Figure not available: see fulltext.]
AB - The aim of the present study was to synthesize isoflavone-enaminones 3a-c and 7-alkoxy-isoflavones 4a-c, evaluate their inhibition of α-glucosidase, and analyze the bioisosteric effect of the presence versus absence of aromatic moieties in these benzopyran derivatives. All the test compounds exhibited greater inhibition of α-glucosidase than the positive control acarbose. The series of isoflavones 3a-c and 4a-c showed higher inhibitory activity (IC50 = 6.3–87.6 µM) than the parental 7-hydroxyisoflavones 2a-c (IC50 = 109.4–173.2 µM), suggesting that the attachment of a 4’-chloroacetophenone moiety to the 7-hydroxyl group of 2a-c is an efficient way to increase the inhibition of α-glucosidase. Furthermore, the aromatic moieties of the series of compounds 3 and 4 enhance inhibitory activity by hydrophobic effects, according to docking calculations. [Figure not available: see fulltext.]
KW - Alkoxy-isoflavones
KW - Diabetes mellitus
KW - Enaminone
KW - Isomaltase
KW - α-Glucosidase
UR - http://www.scopus.com/inward/record.url?scp=85130724370&partnerID=8YFLogxK
U2 - 10.1007/s00044-022-02910-1
DO - 10.1007/s00044-022-02910-1
M3 - Artículo
AN - SCOPUS:85130724370
SN - 1054-2523
VL - 31
SP - 1298
EP - 1312
JO - Medicinal Chemistry Research
JF - Medicinal Chemistry Research
IS - 8
ER -
