Design and synthesis of novel methylene‐bis‐fused pyrazoles as biologically active molecules

Abstract

Abstract magnified image A series of novel methylene‐bis‐fused pyrazoles 12a, 12b, 12c, 12d and methylene‐bis‐2‐(4‐methylsulfonyl)‐phenyl substituted fused pyrazoles 15a, 15b, 15c, 15d have been synthesized by the reaction of methylene‐bis‐aryl‐6‐hydroxymethylene‐2‐cyclohexenones 10 with hydrazine hydrate or (4‐methylsulfonyl)‐phenyl hydrazine 13. Chemical structures of all the newly synthesized compounds were elucidated by their IR, 1H NMR, 13C NMR, and MS spectral data. The compounds 15a, 15b, 15c, 15d were evaluated for their cyclooxygenase‐2 (COX‐2) inhibitory activity, and the compound 15b showed appreciable COX‐2 inhibition and selectivity. Further, all the new compounds were screened for their antimicrobial activity against Gram‐positive, Gram‐negative bacteria, and fungi. Amongst the screened compounds, 12c, 15a, and 15b were found to be the most active against almost all the test bacteria. The compound 15b displayed notable antibacterial activity against Bacillus subtilis (ATCC 6633), Staphylococcus aureus (ATCC 6538p), Micrococcus luteus (IFC 12708), Proteus vulgaris (ATCC 3851), and Salmonella typhimurium (ATCC 14028), equal to that of ampicillin. Similarly, these compounds also showed potent antifungal activity against Candida albicans (ATCC 10231), Aspergillus fumigatus (HIC 6094), Trichophyton rubrum (IFO 9185), and Trichophyton mentagrophytes (IFO 40996). J. Heterocyclic Chem., (2010).