Synthesis of furan tethered 2-pyrazolines via 1,3-dipolar cycloaddition reactions: In vitro evaluation for their antioxidant and antimicrobial activities, molecular docking and ADMET studies

In the present study, we report the synthesis of series of novel substituted pyrazoles via 1,3-dipolar cycloaddition reaction. Nitrile imines generated by the catalytic dehydrogenation of hydrazones by chloramine-T, were trapped in situ by 4-(furan-2-yl)but-3-en-2-one to obtain an isomeric mixture of furan tethered 2-pyrazolines. The new compounds were characterized by 1H NMR, 13C NMR, MS studies and elemental analyses. The synthesized new 2-pyrazolines have been screened in vitro for their antioxidant and antimicrobial activities. Molecular docking and ADMET studies was done to understand the mode of action of synthesized compounds. Among the synthesized series, 1-(3-(4-chlorophenyl)-4-(furan-2-yl)-1-phenyl-4,5-dihydro-1H-pyrazol-5-yl)ethanone 5f, 1-(3-(2,3-dichlorophenyl)-4-(furan-2-yl)-1-phenyl-4,5-dihydro-1H-pyrazol-5-yl)ethanone 5g and 1-(3-(2,4-dichlorophenyl)-4-(furan-2-yl)-1-phenyl-4,5-dihydro-1H-pyrazol-5-yl)ethanone 5hshowed excellent DPPH radical scavenging and antimicrobial potential against the tested bacteria and fungi species.