AUTHOR=Lin Jing , Liang Qi-Ming , Ye Yuan-Na , Xiao Di , Lu Li , Li Meng-Yue , Li Jian-Ping , Zhang Yu-Fei , Xiong Zhuang , Feng Na , Li Chen 

TITLE=Synthesis and Biological Evaluation of 5-Fluoro-2-Oxindole Derivatives as Potential α-Glucosidase Inhibitors

JOURNAL=Frontiers in Chemistry

VOLUME=10

YEAR=2022

URL=https://www.frontiersin.org/journals/chemistry/articles/10.3389/fchem.2022.928295

DOI=10.3389/fchem.2022.928295

ISSN=2296-2646

ABSTRACT=<p>α-Glucosidase inhibitors are known to prevent the digestion of carbohydrates and reduce the impact of carbohydrates on blood glucose. To develop novel α-glucosidase inhibitors, a series of 5-fluoro-2-oxindole derivatives (<bold>3a</bold> ∼ <bold>3v</bold>) were synthesized, and their α-glucosidase inhibitory activities were investigated. Biological assessment results showed that most synthesized compounds presented potential inhibition on α-glucosidase. Among them, compounds <bold>3d</bold>, <bold>3f</bold>, and <bold>3i</bold> exhibited much better inhibitory activity with IC<sub>50</sub> values of 49.89 ± 1.16 μM, 35.83 ± 0.98 μM, and 56.87 ± 0.42 μM, respectively, which were about 10 ∼ 15 folds higher than acarbose (IC<sub>50</sub> = 569.43 ± 43.72 μM). A kinetic mechanism study revealed that compounds <bold>3d</bold>, <bold>3f</bold>, and <bold>3i</bold> inhibited the α-glucosidase in a reversible and mixed manner. Molecular docking was carried out to simulate the affinity between the compound and α-glucosidase.</p>