Synthesis and biological evaluation of 3-(phthalimidomethyl)-4- (5-substituted isoxazoline and pyrazoline) substituted benzanilides

Abstract

3-Phthalimidoethyl benzoic acids 2a-g were prepared by treating N-hydroxy-ethylphthalimide 1 with substituted benzoic acids. The corresponding acid chlorides 3a-g were condensed with 4-aminoacetophenone in the presence of anhydrous potassium carbonate to give 3-phthalimidoethyl-4-acetyl substituted benzanilides 4a-g. The substituted benzanilide derivatives 4a-g were condensed with diverse aromatic aldehydes to afford compounds 5a 1 -d 7 . Compounds 5a 1-7 ...d 1-7 on treatment with hydroxylamine hydrochloride and hydrazine dihydrochloride separately in the presence of sodium acetate afforded titled compounds 6a 1-7 ...d 1-7 and 7a 1-9 . The structures of the newly synthesized compounds have been established by elemental analysis and spectral data and some of the selected compounds have been screened for their antibacterial, antifungal, anthelmintic and hypoglycemic activities.