One-Step Synthesis of 3-(diarylmethyl) indole Derivatives as -glucosidase Inhibitors
Abstract
In this research, a one-step synthesis of 3-(diarylmethyl)indoles (4) via Bi(OTf)3-catalyzed one-pot three-component coupling reaction of indoles, aldehydes and tertiary aromatic amines was developed. After an extensive study, we found that the reaction employing 10 mol% of Bi(OTf)3 under refluxing dichloroethane gave the corresponding 3-(diarylmethyl)indoles (4) in moderate to high yields. The effect of substituents at C-4 position of benzaldehyde derivatives was also studied. The results showed that benzaldehyde derivatives with electron-withdrawing substituents at C-4 position of benzene ring such as Cl, Br and nitro gave the desired products in higher chemical yields than those of electron-donating substituents such as OMe and OH. Furthermore, the synthesized compounds were also evaluated for their a-glucosidase inhibition and the compound 4g exhibited promising a-glucosidase inhibitory activity (65.47 ± 0.22% of inhibition at 1.0 mM).
Keywords : 3-(Diarylmethyl)indoles, Bi(OTf)3, a-Glucosidase inhibitory activity
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