One-pot three-component azide-alkyne cycloaddition: Synthesis of new pyrazole, 1,2,3-triazole,and oxadiazole tethered and their anti-inflammatory,quantitative structure-activity relationship,and docking studies |
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| Authors: | Anish Kumar Kadambar Balakrishna Kalluraya Shalini Singh Vijaykumar Agarwal Bistuvalli Chandrashekarappa Revanasiddappa |
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| Institution: | 1. Department of Studies in Chemistry, Mangalore University, Mangalore, India;2. QSAR & Cheminformatics Laboratory, Department of Chemistry, Bareilly College, Bareilly, India;3. Department of Chemistry, A P S University, Rewa, India;4. Department of Pharmaceutical Chemistry, NGSM Institute of Pharmacy, Mangalore, India |
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| Abstract: | A simple and efficient one-pot three-component azide-alkyne cycloaddition of 5-chloro-1-phenyl-pyrazole-4-carbaldehyde with 2-(prop-2-yn-1-ylthio)-5-(substituted phenoxy)methyl-1,3,4-oxadiazole and sodium azide is reported. The newly synthesized compounds were characterized by spectral and analytical data. They were screened for in vitro anti-inflammatory activity by bovine serum albumin denaturation assay. All the tested compounds showed moderate anti-inflammatory activity, whereas three compounds ( 4d , 4i , and 4k ) showed excellent activity comparable with that of the standard drug diclofenac sodium. The quantitative structure-activity relationship (QSAR) study was carried out for anti-inflammatory activities of the synthesized compounds and developed a QSAR model. Inspired by their in vitro anti-inflammatory activities, they were docked to the active site of COX-2 to know the anti-inflammatory potency in silico. |
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