Synthesis, characterization and in vitro biological screening of 4-hydroxy naphthalen-1-yl, naphtho[1,2-b]furan, benzo[h]chromene and 5,6-dihydropyridazine derivatives containing sulfonamide moiety

Abstract

In this study, a series of 4-((4-hydroxynaphthalen-1-yl)diazenyl)benzenesulfonamides have been prepared by subsequent diazotization of sulfonamide derivatives and coupling with 1-naphthol in alkaline medium. Cyclization of 4-((4-hydroxynaphthalen-1-yl)diazenyl)benzenesulfonamides with cinnamic acid in the presence of a basic catalyst afforded the novel naphtho[1,2-b]furans. Also, 4-((4-hydroxynaphthalen-1-yl)diazenyl)benzenesulfonamides can be cyclized with α-cyanocinnamonitriles to afford 2-amino-3-cyano-4-phenyl-4H-benzo[h]chromenes. 4-(4-amino-3,5-dicyano-6-iminopyridazin-1(6H)-yl)benzenesulfonamides were obtained at room temperature by treatment of 2-amino-1,1,3-tricyanopropene with a diazonium salt of sulfonamide derivatives. The structures of newly synthesized compounds were confirmed by analytical data and spectroscopic techniques. The antimicrobial activity of the obtained compounds was assessed in vitro by qualitative and quantitative (minimum inhibitory concentration) (MIC) assays.