European Journal of Chemistry

Design and synthesis of new coumarin-1,2,3-triazole hybrids as new antidiabetic agents: In vitro α-amylase, α-glucosidase inhibition, anti-inflammatory, and docking study

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Vinayaka Chandrappa Barangi
Lokesh Anand Shastri
Prakasha Kothathi Chowdegowda
Rohini Sangappanavar
Karthik Inamdar
Nagarjuna Prakash Dalbanjan
Delicia Avilla Barretto
Vinay Sunagar

Abstract

The current study focuses on the synthesis of coumarin-triazole hybrids (7i-t) starting from 4-hydroxy benzaldehyde or 4-hydroxyacetophenone (1a-b) and propargyl bromide. On the other hand, coumarin derivatives (5c-h) were prepared by Pechmann cyclization and treated with sodium azide to give the corresponding 3-azido methyl coumarins (6c-h). Finally, 1,3-dipolar cycloaddition between compounds 6c-h and terminal alkyne 2a-b produces coumarin-triazole hybrids (7i-t) utilizing click chemistry approaches that are high yielding, wide in scope and simple to perform. The structural proofs of the newly synthesized coumarin-triazole hybrids (7i-t) are proved by various spectroscopic techniques, including IR, 1H NMR, 13C NMR, and LC-MS. The synthesized new coumarin triazole hybrids (7i-t) were explored for their antihyperglycemic potential and therefore evaluated for α-glucosidase and α-amylase inhibitory activities along with anti-inflammatory. The results suggest that among the series, compound 7l showed excellent activity with an IC50 value of 0.67±0.014 mg/mL and 0.72±0.012 mg/mL for α-amylase, and α-glucosidase inhibitory potential while compound 7o showed promising anti-inflammatory activity with IC50 value of 0.54±0.003 mg/mL. To support the above findings, molecular docking studies were performed, which confirmed the interaction of the synthesized molecules 7i-t with an effective binding energy of -9.0 to -10.6 kcal/mol at the active site of the enzyme human pancreatic α-amylase (PDB ID: 1B2Y). Therefore, these scaffolds have the potential to function as lead candidates for antidiabetic and anti-inflammatory activities.


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Barangi, V. C.; Shastri, L. A.; Chowdegowda, P. K.; Sangappanavar, R.; Inamdar, K.; Dalbanjan, N. P.; Barretto, D. A.; Sunagar, V. Design and Synthesis of New Coumarin-1,2,3-Triazole Hybrids As New Antidiabetic Agents: In Vitro α-Amylase, α-Glucosidase Inhibition, Anti-Inflammatory, and Docking Study. Eur. J. Chem. 2024, 15, 205-219.

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Supporting Agencies

Karnatak University, Dharwad-580003, Karnataka, India, Council of Scientific and Industrial Research-University Grant Commission (CSIR-UGC) fellowship (Ref. No.: 151674 Roll. No. DEC: 2018-2019), University Scientific Instrumentation centre (USIC) and the Sophisticated Analytical Instrument Facilities-Department of Science and Technology (SAIF-DST) of Karnatak University, Dharwad, India
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