TY - JOUR
T1 - Synthesis and biological evaluation of novel chromonyl enaminones as α-glucosidase inhibitors
AU - Mendieta-Moctezuma, Aarón
AU - Rugerio-Escalona, Catalina
AU - Villa-Ruano, Nemesio
AU - Gutierrez, Rsuini U.
AU - Jiménez-Montejo, Fabiola E.
AU - Fragoso-Vázquez, M. Jonathan
AU - Correa-Basurto, José
AU - Cruz-López, María C.
AU - Delgado, Francisco
AU - Tamariz, Joaquín
N1 - Publisher Copyright:
© 2019, Springer Science+Business Media, LLC, part of Springer Nature.
PY - 2019/6/1
Y1 - 2019/6/1
N2 - Series of novel chromonyl enaminones 1a–e and 2a–e and 3-alkylated chromones 3a–e were synthesized and evaluated in vitro as α-glucosidase inhibitors as well as antioxidant and antifungal agents. Antifungal activity was tested on strains of Candida albicans. Compounds 2a and 2d–e showed good inhibition of the α-glucosidase enzyme (IC50 = 5.5, 0.9, and 1.5 mM, respectively), their effect being better than that of 1a–e, 3a–e, and acarbose (the standard, IC50 = 7.73 ± 0.9 mM). The structure–activity relationship suggests that the phenyl group at the C-3 position of the chromone ring system and the 4-chlorophenyl group at the enaminone moiety (derivatives 2) increased the inhibition of α-glucosidase. Compounds 2a–e exhibited a slight antioxidant effect, and compounds 3a–e a moderate antifungal activity against C. albicans (IC50 70.5–83.1 µg/mL). Docking studies revealed that compounds 2 interact with the α-glucosidase residues of the binding pocket. Therefore, these chromone derivatives may be considered as potential α-glucosidase inhibitors, as well as antifungal agents against some Candida strains of yeast.
AB - Series of novel chromonyl enaminones 1a–e and 2a–e and 3-alkylated chromones 3a–e were synthesized and evaluated in vitro as α-glucosidase inhibitors as well as antioxidant and antifungal agents. Antifungal activity was tested on strains of Candida albicans. Compounds 2a and 2d–e showed good inhibition of the α-glucosidase enzyme (IC50 = 5.5, 0.9, and 1.5 mM, respectively), their effect being better than that of 1a–e, 3a–e, and acarbose (the standard, IC50 = 7.73 ± 0.9 mM). The structure–activity relationship suggests that the phenyl group at the C-3 position of the chromone ring system and the 4-chlorophenyl group at the enaminone moiety (derivatives 2) increased the inhibition of α-glucosidase. Compounds 2a–e exhibited a slight antioxidant effect, and compounds 3a–e a moderate antifungal activity against C. albicans (IC50 70.5–83.1 µg/mL). Docking studies revealed that compounds 2 interact with the α-glucosidase residues of the binding pocket. Therefore, these chromone derivatives may be considered as potential α-glucosidase inhibitors, as well as antifungal agents against some Candida strains of yeast.
KW - Candida albicans
KW - Chromones
KW - Chromonyl enaminones
KW - α-glucosidase inhibitors
UR - http://www.scopus.com/inward/record.url?scp=85064261627&partnerID=8YFLogxK
U2 - 10.1007/s00044-019-02320-w
DO - 10.1007/s00044-019-02320-w
M3 - Artículo
SN - 1054-2523
VL - 28
SP - 831
EP - 848
JO - Medicinal Chemistry Research
JF - Medicinal Chemistry Research
IS - 6
ER -