Synthesis of diverse novel compounds with anticipated antitumor activities starting with biphenyl chalcone

Abstract

The chalcone as (E)-1-([1,1′-biphenyl]-4-yl)-3-(3,4-dimethoxyphenyl)prop-2-en-1-one (3) was reacted with various active methylene compounds via Michael addition reaction under different conditions. In one hand, chalcone 3 reacted with isatin and glycine in one pot reaction via 1,3-dipolar cycloaddition reaction. On the other hand, chalcone 3 was also reacted with different N-nucleophiles via direct addition on the carbonyl group to award cyclic and/or acyclic products. Meanwhile, the reaction of chalcone 3 with S-benzylthiuronium chloride afforded the thio-Michael addition product. Chalcone 3 and 10 novel synthesized compounds were screened against two cell lines (HepG2 and MCF-7). Among of them, thiosemicarbazone 16, oxime 14 and pyrimidine-2(1H)-thione 19 derivatives revealed an excellent activity against both cell lines (IC50 values = 6.79-12.91 μM), whereas thiosemicarbazone 16 (6.79 ± 0.5 and 7.58 ± 0.6 μM) showed the highest activity.