Synthesis, Cytotoxic, and Antioxidant Activity of Some Benzoquinoline-Based Heterocycles

Abstract

A series of benzoquinoline-based heterocycles was synthesized using 2-((3-chlorobenzo[f]quinolin-2-yl)methylene)hydrazine-1-carbothioamide as a key material via condensation of 3-chlorobenzo[f]quinoline-2-carbaldehyde with thiosemicarbazide. The titled thiosemicarbazone scaffold was conducted with some carbon electrophilic reagents such as acetic anhydride, chloroacetyl chloride, chloroacetic acid, 2-bromo-1-(3-nitrophenyl)ethan-1-one, 2-chloro-N-phenylacetamide, and dimethyl but-2-ynedioate to obtain triazole thione, imidazolone, thiazolidinone, and thiazole derivatives. On the other hand, hydrazinolysis of thiosemicarbazone did not proceed as expected but it gave the azine derivative. The in vitro antitumor and antioxidant activity of the synthesized compounds were screened and revealed that triazole thione and thiazole derivatives were the most potent.