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oai:ojs.www.eurjchem.com:article/2541 2024-09-30T08:57:10Z eurjchem:ART driver

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 Barangi, Vinayaka Chandrappa Shastri, Lokesh Anand Chowdegowda, Prakasha Kothathi Sangappanavar, Rohini Inamdar, Karthik Dalbanjan, Nagarjuna Prakash Barretto, Delicia Avilla Sunagar, Vinay Diabetes Triazoles Coumarins Inflammation Alpha-amylase Alpha-glucosidase 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. Atlanta Publishing House LLC 2024-09-30 info:eu-repo/semantics/article info:eu-repo/semantics/publishedVersion application/pdf https://www.eurjchem.com/index.php/eurjchem/article/view/2541 10.5155/eurjchem.15.3.205-219.2541 European Journal of Chemistry; Vol. 15 No. 3 (2024): September 2024; 205-219 2153-2257 2153-2249 eng https://www.eurjchem.com/index.php/eurjchem/article/view/2541/2837 Copyright (c) 2024 Vinayaka Chandrappa Barangi, Lokesh Anand Shastri, Prakasha Kothathi Chowdegowda, Rohini Sangappanavar, Karthik Inamdar, Nagarjuna Prakash Dalbanjan, Delicia Avilla Barretto, Vinay Sunagar https://creativecommons.org/licenses/by-nc/4.0