Synthesis and in vitro antimicrobial evaluation of novel fluorine-containing 3-benzofuran-2-yl-5-phenyl-4,5-dihydro-1H-pyrazoles and 3-benzofuran-2-yl-5-phenyl-4,5-dihydro-isoxazoles

Abstract

In the present study, some novel fluorine-containing heterocycles incorporating benzofuran with dihydropyrazoles and dihydroisoxazoles have been synthesized and evaluated for their in vitro antibacterial and antifungal activities. 2-Acetylbenzofuran on treatment with fluorinated aldehydes afforded corresponding fluorine-containing 1-benzofuran-2-yl-3-phenyl-prop-2-en-1-ones (chalcones 5a–g). The cyclocondensation of chalcones (5a–g) with hydrazine hydrate under basic conditions resulted in formation of corresponding novel fluorine-containing 3-benzofuran-2yl-5-phenyl-4,5-dihydro-1H-pyrazoles (6a–g). Similar reaction with hydroxylamine hydrochloride yielded 3-benzofuran-2yl-5-phenyl-4,5-dihydro-isoxazoles (7a–g). All the synthesized compounds have been characterized on the basis of analytical and spectral data, and were screened for their antibacterial and antifungal activities. Some of the synthesized compounds showed good antibacterial and antifungal activities.