Synthesis and Antimicrobial Activity of Some (Nitro)furfurylidene-Containing Hexahydroindazoles

Abstract

Data on the synthesis and antimicrobial activity of some furfurylidene-containing hexahydroindazoles with pharmacophore fragments (furan and pyrazoline cycles, nitro-, azomethine, and other groups) are presented. The target hexahydroindazoles were obtained with 74 – 90% yields using reactions of hydrazines (hydrazine hydrate, phenylhydrazine) with nonsymmetric 2-furfurylidene-6-arylidenecyclohexanones with or without electron donor/acceptor substituents in the furan (CH3, NO2) and phenyl (3-NO2) cycles. The structure of the synthesized compounds was established by IR and 1H and 13C NMR spectroscopy. The synthesized hexahydroindazoles and chalcones exhibit antimicrobial activity against St. aureus, E. coli, Pr. mirabilis, and Ps. aeruginosa. In particular, 2,3-diphenyl-7-(5-nitrofurfurylidene)-3,3a,4,5,6,7-hexahydroindazole exhibits a high selectivity with respect to St. aureus.