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 (CH 3 , NO 2 ) and phenyl (3-NO 2 ) cycles. The structure of the synthesized compounds was established by IR and 1 H and 13 C 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.

Reactions of 1-aryl- and 2,3-diaryl- 5-diazo-6,6-dimethyl-4-oxo-4,5,6,7-tetra- hydroindazoles with N-ethyl- and N-phenyl-substituted maleimides

“…This is the result of the varied biological action of a large number of synthesized indazole derivatives. Among them have been discovered agonists and antagonists of estrogen receptors [9,10], dopamine D-3 [11,12], corticotropin [13], and adenosine [14]; derivatives have been found with antitumor [15], antiinflammatory [16], and antimicrobial [17] action; inhibitors of HIV proteases [18] and membrane-active substances [19] have been discovered. Indazole derivatives have also been used as ligands [20].…”