Ultrasound promoted synthesis of N-(substituted phenyl)-2-(7‑hydroxy-4-methyl-2H-chromen-2-ylidene)hydrazine-1-carboxamides as cytotoxic and antioxidant agents

摘要: Abstract New N-(substituted phenyl)-2-(7-hydroxy-4-methyl-2H-chromen-2-ylidene)hydrazine-1-carboxamides (5a-l) was synthesized in two steps using environmentally friendly ultrasound irradiation. The first step involved solvent free synthesis of 7-hydroxy-4-methyl-2H-chromen-2-one (3) by catalytic amount (10% mol) FeCl3. second condensation intermediate 3 and hydrazine carboxamide HCl analogues (4a-l) under ultrasonic influence the water-ethanol (2:1) system to obtain title compounds good yield. structure prepared confirmed spectroscopic study. synthetic strategy described here has many advantages, including a simple procedure high conversion with quick reaction times. cytotoxicity tested on 60 NCI cancer cell lines at 10 µM N-(4-chlorophenyl)-2-(7-hydroxy-4-methyl-2H-chromen-2-ylidene)hydrazine-1-carboxamide (5b) showed promising activity maximum sensitivity against CCRF-CEM, UO-31, RPMI-8226, NCI-H522, HL-60(TB) growth percent (GP) 17.50, 79.67, 80.59, 82.35, 83.70 respectively. In DPPH radical scavenging assay, 5b 5d antioxidant IC50 values 16.32±1.29 14.28±1.82 M, binding affinity target ligands active site FGFR also investigated molecular docking. Within FGFR4, ligand interacted four H-bonds Asp630 (carbonyl function), Glu520 (with amide NH ArNH), Ile609 (phenol while an imine “N” salt bridges Glu520.