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Design, synthesis, in vitro, and in silico biological evaluations of coumarin-indole hybrids as new anti-α-glucosidase agents. 2022

Davood Rezapour Niri, and Mohammad Hosein Sayahi, and Somayeh Behrouz, and Ali Moazzam, and Somayeh Mojtabavi, and Mohammad Ali Faramarzi, and Bagher Larijani, and Hossein Rastegar, and Maryam Mohammadi-Khanaposhtani, and Mohammad Mahdavi
Medicinal Chemistry Research Laboratory, Department of Chemistry, Shiraz University of Technology, Shiraz, Iran.

BACKGROUND A series of coumarin-indole hybrids was synthesized as the new α-glucosidase inhibitors. The title hybrids were considered as α-glucosidase inhibitors because had two active pharmacophores against α-glucosidase: coumarin and indole. METHODS The thirteen various derivatives 4a-m were synthesized, purified, and fully characterized. These compounds were evaluated against α-glucosidase in vitro and in silico. In silico pharmacokinetic studies of the most potent compounds were also performed. RESULTS Most of the title compounds exhibited high anti-α-glucosidase activity in comparison to standard drug acarbose. In particular, the phenoxy derivative 4d namely 3-((1H-indol-3-yl)(3-phenoxyphenyl)methyl)-4-hydroxy-2H-chromen-2-one showed promising activity. This compound is a competitive inhibitor against α-glucosidase and showed the lowest binding energy at the α-glucosidase active site in comparison to other potent synthesized compounds and acarbose. CONCLUSIONS Compound 4d can be a lead compound for further structural development to obtain effective and potent α-glucosidase inhibitors.

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