Synthesis and antitumor activity evaluation of some pyrrolone and pyridazinone heterocycles derived from 3-((2-oxo-5-(p-tolyl)furan-3(2H)-ylidene)methyl)quinolin-2(1H)-one

Abstract

The broad spectrum of biological activity of quinoline derivatives coupled with our interest in the chemistry of furanones led us to synthesize a quinoline derivative bearing a 2(3H)-furanone scaffold. This derivative was used as a key starting material for the construction of some pyrrolone, imidazole, and pyridazinone derivatives obtained by reactions with some nitrogen nucleophiles viz. ammonium acetate, benzylamine, 1,2-diaminoethane, and hydrazine hydrate. The hydrazide obtained was condensed with 3-chlorobenzaldehyde, 1,3-diphenyl-1H-pyrazole-4-carbaldehyde, isatin, and dodecanoyl chloride to achieve the corresponding hydrazone and pyrrolone derivatives. Also, the synthesized compounds were evaluated for their in vitro antitumor activity using two cancer cell lines: breast and colon tumors. Some compounds displayed satisfactory activities.

Graphical Abstract

Keywords:

• Cytotoxicity
• furanone
• pyridazinone
• pyrrolone
• quinoline