A new series of 32 derivatives of 4-pyrazolyl-N-(hetero)arylquinoline 5a-p and 6a-p were synthesized by a one-pot base-catalyzed cyclocondensation reaction of 1-phenyl-3-(hetero)aryl-pyrazole-4-carbaldehyde 1a-h, malononitrile 2, and 3-(hetero)aryl-5,5-disubstitutedcyclohex-2-enone 3a-b or 4a-b, respectively. All the synthesized compounds were characterized by elemental analysis, FT-IR, (1) H-NMR, and (13) C-NMR spectral data. All the synthesized compounds were screened, against six bacterial pathogens, namely Bacillus subtilis, Clostridium tetani, Streptococcus pneumoniae, Salmonella typhi, Vibrio cholerae, Escherichia coli, and antifungal activity, against two fungal pathogens Aspergillus fumigatus and Candida albicans, using broth microdilution MIC method. Some of the compounds were found to be more or equipotent against most of the employed strains than commercially available drugs as evident from the screening data.
A new series of pyrazolo [1,2-b]phthalazine derivatives (4a-p) bearing the 5-aryloxypyrazole nucleus was synthesized by one-pot, three-component, base-catalyzed cyclo condensation reaction of 3-methyl-5-aryloxy-1-aryl-1H-pyrazole-4-carbaldehyde (1a-d), malononitrile or ethyl cyanoacetate (2a-b) and 2,3-dihydro-1,4-phthalazinedione (3a-b) in ethanol containing an eco friendly base, NaOH, in good to excellent yields. All synthesized compounds (4a-p) were duly characterized by physicochemical parameters, 1 H NMR, 13 C NMR, FT-IR and LCMS techniques. In vitro antimicrobial activity of the synthesized compounds was investigated against a representative panel of pathogenic strains. Compounds 4e, 4g, 4h, 4k and 4o exhibited excellent antimicrobial activity compared with first line drugs. In vitro antituberculosis activity was evaluated against Mycobacterium tuberculosis H37Rv, and compounds 4g and 4o emerged as the promising antimicrobial members with better antituberculosis activity. A brine shrimp bioassay was carried out to study the in vitro cytotoxic properties of the synthesized compounds. In vitro antioxidant activity was evaluated by the ferricreducing antioxidant power method. Compounds 4c, 4d, 4g and 4h showed the highest antioxidant potencies.
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