Multicomponent reaction for the synthesis of new 1,3,4-thiadiazole-thiazolidine-4-one molecular hybrids as promising antidiabetic agents through α-glucosidase and α-amylase inhibition.
Bioorg Chem
; 115: 105210, 2021 10.
Article
en En
| MEDLINE
| ID: mdl-34332231
ABSTRACT
A simple and efficient protocol was developed to synthesize a new library of thiazolidine-4-one molecular hybrids (4a-n) via a one-pot multicomponent reaction involving 5-substituted phenyl-1,3,4-thiadiazol-2-amines, substituted benzaldehydes and 2-mercaptoacetic acid. The synthesized compounds were evaluated in vitro for their antidiabetic activities through α-glucosidase and α-amylase inhibition as well as their antioxidant and antimicrobial potentials. Compound 4e exhibited the most promising α-glucosidase and α-amylase inhibition with an IC50 value of 2.59 µM, which is ~1.5- and 14-fold superior as compared to the standard inhibitor acarbose. Structure-activity relationship (SAR) analysis revealed that the nature and position of substituents on the phenyl rings had a significant effect on the inhibitory potency.
Palabras clave
Texto completo:
1
Banco de datos:
MEDLINE
Asunto principal:
Tiadiazoles
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Alfa-Amilasas
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Alfa-Glucosidasas
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Tiazolidinas
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Inhibidores de Glicósido Hidrolasas
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Hipoglucemiantes
Límite:
Humans
Idioma:
En
Año:
2021
Tipo del documento:
Article