Synthesis and antiproliferative activity of 4H-chromonephenylhydrazones, 1H-pyrazolecarboxylates and pyrazolylmethanones

Abstract

Series of 4H-chromone-based hydrazones 3a–z, pyrazolecarboxylates 5a–x and pyrazolylmethanones 6a–u were prepared and screened for their anti-proliferative activity on A549, HeLa, DU145 and MDAMB 231 cell lines. The hydrazone compound 3s with a chloro substituent on the chromanone moiety and a methoxy group on the phenyl ring displayed promising activity on A549, HeLa and DU145 cell lines. The compound 5p with a bromo substituent on the chromanone moiety and a methyl group on the phenyl ring displayed potent activity on DU145. Furopyrazolecarboxylate 5w having a methyl substituent on the phenyl ring displayed potent activity on HeLa cell line. The pyrazolylmethanone 6e with a fluoro substituent on the phenyl ring and compound 6j having a methyl substituent on the chromanone moiety and a methoxy group on the phenyl ring have shown promising anti-proliferative activity on HeLa cell line.

Keywords

• 3-Formylchromones
• 1H-pyrazolecarboxylates
• 1H-pyrazolylmethanones
• cycloaddition and antiproliferative activity