Microwave-assisted copper( i ) catalyzed A 3 cascade coupling of imidazo[1,2- a ]pyridines via C–H bond functionalization as selective COX-2 inhibitors and antioxidants, and in silico studies
A proficient copper( i ) catalyzed three-component synthetic protocol has been established for the synthesis of medicinally essential substituted imidazo[1,2- a ]pyridines by means of C–H bond amination followed by acetylene incorporation under microwave irradiation. The biological results and compu...
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Published in | New journal of chemistry Vol. 47; no. 19; pp. 9401 - 9413 |
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Main Authors | , , , , , , |
Format | Journal Article |
Language | English |
Published |
16.05.2023
|
Online Access | Get full text |
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Summary: | A proficient copper(
i
) catalyzed three-component synthetic protocol has been established for the synthesis of medicinally essential substituted imidazo[1,2-
a
]pyridines by means of C–H bond amination followed by acetylene incorporation under microwave irradiation. The biological results and computational analysis suggested that the compounds had a greater affinity for the COX-2 enzyme than for the COX-1 enzyme. The investigation of docked (PDB ID: 5IKR; A-chain) postures of the compounds exemplified that they embrace similar configurations to the exceedingly selective COX-2 inhibitor. The compounds 8e, 8h, 8l, 8n, 8p, 8r, 8t, 8v and 8x originated as the most efficient and selective COX-2 inhibitors with IC
50
values of 18.94, 0.02, 3.28, 0.067, 0.05, 19.42, 3.66, 0.19 and 24.59 μg mL
−1
respectively in contrast to mefenamic acid (25.74 μg mL
−1
). The selectivity index was obtained for all the significantly active molecules. Excitingly, the molecules that were effective as COX-2 inhibitors were active as antioxidant agents as well. |
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ISSN: | 1144-0546 1369-9261 |
DOI: | 10.1039/D3NJ00524K |