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Three groups of novel analogs of combretastatin-A4 (CA-4), viz., the N1-phenyl-pyrazoline (5a–e), N1-alkyl acetylated pyrazoline (6a–c), and N1-phenyl acetylated pyrazoline (7a–g) were designed, and synthesized in good yield. The structure of the compounds was confirmed by spectroscopic techniques. All the compounds were evaluated for their in vitro anticancer (MCF-7 cell line), antioxidant (DPPH, NO, SOR, and H2O2), and anti-inflammatory activity. Compounds 5d, 7g, 7f, 7e, 7c, 5b, 6a, 7b, and 7a showed excellent potency with GI50 ranging from 0.1 to 10.9 µM against the MCF-7 cell line. Compounds 7f, 7g, 5c, 5d, 5b, 7e, and 6a exhibited good anti-inflammatory activity. Encouraged by these results, all the compounds were also tested for their antioxidant potency. Compounds 6a, 6c, 7b, 7c, 7f, and 7g were found to be excellent scavengers of all four free radicals (DPPH, NO, SOR, and H2O2). [ABSTRACT FROM AUTHOR]

In the present research work, ultrasound-assisted synthesis of a series of novel azomethine derivatives of 1-phenylimidazo[1,5-a]pyridine has been achieved. The synthetic route involves the conversion of ethyl-1-phenylimidazo-[1,5-a]pyridine-3-carboxylate to 1-phenylimidazo[1,5-a]pyridine-3-carbohydrazide followed by nucleophilic addition-elimination reaction with diverse aromatic aldehydes. The developed clean and simple protocol offers a set of advantages such as mild reaction conditions, environment friendliness, and high atom economy apart from excellent yields (70–92%). All compounds were found to be stable in atmospheric conditions for a long period of time and were soluble in polar solvents. [ABSTRACT FROM AUTHOR]