Synthesis, characterization, and antidiabetic activity of 6‐methoxyimidazo[1,2‐b]pyridazine derivatives

• Published in: Journal of the Chinese Chemical Society (Taipei) Vol. 66; no. 6; pp. 630 - 637
• Main Authors: Kota, Tata Veereswara Rao, Gandham, Himabindu, Sanasi, Paul Douglas
• Format: Journal Article
• Language: English
• Published: Weinheim Wiley‐VCH Verlag GmbH & Co. KGaA 01.06.2019
• Subjects: 6‐methoxyimidazo[1,2‐b]pyridazine; antidiabetic; Suzuki reaction; zinc oxide nanoparticles
• ISSN: 0009-4536; 2192-6549
• DOI: 10.1002/jccs.201800332

The present article describes the synthesis, characterization, and antidiabetic activity of 6‐methoxyimidazo[1,2‐b]pyridazine derivatives 7a‐l. The synthetic sequence for the preparation of these derivatives involves the following prominent reactions: (a) Step 1: involves the high‐pressure amination reaction; (b) Step 2: involves the Zinc oxide nanoparticle‐catalyzed cyclization reaction; (c) Step 3: involves the methoxylation; (d) Step 4: involves the bromination reaction; (e) Step 5: involves the Suzuki coupling reaction; (f) Step 6: involves the reduction of the –NO2 group; (g) Step 7: involves Boc protection of the 1o amino group (h) Step 8: involves diazotization of the amine group and finally the last of the synthesis (i) Step 9: involves the saponification of the ethyl ester group. Furthermore, the structures of the newly synthesized 6‐methoxyimidazo[1,2‐b]pyridazine derivatives 7a–l were determined using 1H NMR, 13C NMR, and Mass and IR spectroscopic analyses. These derivatives were evaluated for their antidiabetic property and the results revealed that most of the compounds exhibited significant potency. It is worth mentioning that compounds 7b (69.87%), 7f (69.0%), 7h (68.79%), and 7l (68.61%) with substitution R = para‐NH2, para‐COOH, meta‐NH2, and meta‐COOH, respectively, showed significant (good) hypoglycemic activity when compared to the standard drug insulin (50 mg/kg b.w) in reducing the blood glucose level. The present work describes the synthesis, characterization, and antidiabetic activity of 6‐methoxyimidazo[1,2‐b]pyridazine derivatives 7a‐l. These compounds were characterized using 1H NMR, 13C NMR, Mass, IR spectroscopic analysis, and Elemental analysis. These derivatives were evaluated for their antidiabetic properties and the results revealed that most of the compounds exhibited significant potency when compared to the standard drug insulin.