Accessing anti-human lung tumor cell line (A549) potential of newer 3,5-disubstituted pyrazoline analogs

Abstract

A new series of pyrazoline analogs was furnished and evaluated for their in vitro anticancer efficacies against human non-small-cell lung cancer cell line A549. Claisen–Schmidt condensation between intended acetophenone compound and different substituted aldehydes resulted in the formation of corresponding chalcones which were cyclized using hydrazine hydrate to yield the final pyrazoline intermediates. α-Naphthyl isothiocyanate was prepared from benzoyl chloride and α-naphthyl amine through α-naphthyl thiourea to react with pyrazoline intermediates to furnish title compounds 10a–h, disubstituted pyrazolines in good yields and purity. All final analogs were screened for their anticancer potential using MTT and SRB assay in addition to the determination of their cytotoxic nature. Final compounds revealed a good deal of potential against A549 cell lines with reasonable level of cytotoxic nature, particularly analogs with fluorine and thiomethyl and methoxy functional group demonstrated good potencies. SAR showed that the activity level varied with the variation in the nature of substituent present on the phenyl ring attached to the C-4 position of the pyrazoline ring. This study revealed the efficacies of presented molecules for further development as anticancer congeners. The structures of final compounds were confirmed with the aid of FT-IR, 1H NMR, 13C NMR spectroscopy and CHN analysis.

Keywords

• 3,4,5-Trimethoxy acetophenone
• Aldehydes
• α-Naphthyl isothiocyanate
• Pyrazoline
• Lung cancer
• Anticancer activity