Synthesis of 6-chloro-2-Aryl-1H-imidazo[4,5-b]pyridine derivatives: Antidiabetic, antioxidant, β-glucuronidase inhibiton and their molecular docking studies

• Published in: Bioorganic Chemistry
• Main Author: Taha M.; Ismail N.H.; Imran S.; Rashwan H.; Jamil W.; Ali S.; Kashif S.M.; Rahim F.; Salar U.; Khan K.M.
• Format: Article
• Language: English
• Published: Academic Press Inc. 2016
• Online Access: https://www.scopus.com/inward/record.uri?eid=2-s2.0-84958996989&doi=10.1016%2fj.bioorg.2016.01.007&partnerID=40&md5=cf0be1f737f4e6e84767bb66c00023a9

6-Chloro-2-Aryl-1H-imidazo[4,5-b]pyridine derivatives 1-26 were synthesized and characterized by various spectroscopic techniques. All these derivatives were evaluated for their antiglycation, antioxidant and β-glucuronidase potential followed their docking studies. In antiglycation assay, compound 2 (IC50 = 240.10 ± 2.50 μM) and 4 (IC50 = 240.30 ± 2.90 μM) was found to be most active compound of this series, while compounds 3 (IC50 = 260.10 ± 2.50 μM), 6 (IC50 = 290.60 ± 3.60 μM), 13 (IC50 = 288.20 ± 3.00 μM) and 26 (IC50 = 292.10 ± 3.20 μM) also showed better activities than the standard rutin (IC50 = 294.50 ± 1.50 μM). In antioxidant assay, compound 1 (IC50 = 69.45 ± 0.25 μM), 2 (IC50 = 58.10 ± 2.50 μM), 3 (IC50 = 74.25 ± 1.10 μM), and 4 (IC50 = 72.50 ± 3.30 μM) showed good activities. In β-glucuronidase activity, compounds 3 (IC50 = 29.25 ± 0.50 μM), compound 1 (IC50 = 30.10 ± 0.60 μM) and compound 4 (IC50 = 46.10 ± 1.10 μM) showed a significant activity as compared to than standard D-Saccharic acid 1,4-lactonec (IC50 = 48.50 ± 1.25 μM) and their interaction with the enzyme was confirm by docking studies. © 2016 Elsevier Inc. All rights reserved.