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Synthesis of diverse novel compounds with anticipated antitumor activities starting with biphenyl chalcone
Author(s) -
Ismail Mahmoud F.,
Elsayed Amira A.
Publication year - 2020
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.4017
Subject(s) - chalcone , chemistry , isatin , oxime , thio , methylene , semicarbazone , pyrimidine , michael reaction , medicinal chemistry , biphenyl , stereochemistry , organic chemistry , catalysis
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(1 H )‐thione 19 derivatives revealed an excellent activity against both cell lines (IC 50 values = 6.79‐12.91 μM), whereas thiosemicarbazone 16 (6.79 ± 0.5 and 7.58 ± 0.6 μM) showed the highest activity.