Synthesis, biological activity and molecular docking study of some new chalcones, pyrazolines and isoxazolines derivatives bearing 1,2,3- triazoline

Abstract

In this work a variety of new compounds such as chalcones, pyridine and isooxazoline derivatives has been synthesized. 2-((1-(4-acetylphenyl)-4,5-dihydro-1H-1,2,3-triazol-4-yl)methyl)benzo[d]isothiazol-3(2H)-one 1,1-dioxide(1) have been chosen as a starting material. Condensation of compound(1) with aromatic aldehydes namely benzaldehyde, p-chloro benzaldehyde, p-bromo benzaldehyde, p-nitro benzaldehyde, p-hydroxy benzaldehyde, m-hydroxy benzaldehyde, p-N,N-dimethyl benzaldehyde and 2,4-dimethoxy benzaldehyde in the presence of 40% KOH gave chalcone derivatives (2a-h). The cyclization of prepared chalcone derivatives semicarbazide in the presence acetic acid product pyrazoline derivatives(3a-f). Reaction of chalcone derivatives(2a-h) with hydroxylamine hydrochloride in the presence of sodium acetate afforded corresponding isooxazoline derivatives (4a-d). FT-IR, 1HNMR, and 13CNMR were used to characterize the target compounds. The results showed that the target compounds have a good biological activity such as antibacterial and antioxidant. The molecular docking studies of the target 6ul7 with the newly synthesized compounds showed good docking scores with acceptable binding interactions. The present results reveal that the newly synthesized compounds exhibit promising inhibition activity against Escherichia Coli.