Synthesis, characterization and pharmacological activities of 2-[4-cyano-(3-trifluoromethyl)phenyl amino)]-4-(4-quinoline/coumarin-4-yloxy)-6-(fluoropiperazinyl)-s-triazines

A series of 2-[4-cyano-(3-trifluoromethyl)phenyl amino)]-4-(4-quinoline/coumarin-4-yloxy)-6-(fluoropiperazinyl)-s-triazines has been synthesized by a simple and efficient synthetic protocol. The antimicrobial activity of the compounds was studied against several bacteria (Staphylococcus aureus MTCC 96, Bacillus cereus MTCC 619, Escherichia coli MTCC 739, Pseudomonas aeruginosa MTCC 741, Klebsiella pneumoniae MTCC 109, Salmonella typhi MTCC 733, Proteus vulgaris MTCC 1771, Shigella flexneria MTCC 1457) and fungi (Aspergillus niger MTCC 282, Aspergillus fumigatus MTCC 343, Aspergillus clavatus MTCC 1323, Candida albicans MTCC 183) using paper disc diffusion technique and agar streak dilution method. Newly synthesized compounds were also tested for their in vitro antimycobacterial activity against Mycobacterium tuberculosis H37Rv using BACTEC MGIT and Lowenstein–Jensen MIC method.

Graphical abstractThe work focused on design, synthesis, characterization and determination of antibacterial efficacy of new fluorinated s-triazinyl piperazines. Influence of the presence and absence of fluorine group on the biological profile of the resultant molecules was also discussed. Several s-triazines showed a good deal of activity against the full array of bacterial and fungal strains at the MIC ranging from 3.12 to 100 μg/mL.Figure optionsDownload full-size imageDownload as PowerPoint slideHighlights► A series of novel s-triazine analogues incorporating fluoro-piperazines has been synthesized. ► Compounds were screened for their in vitro antimicrobial and antimycobacterial activities. ► New compounds are characterized adequately by FT-IR, 1H NMR, 13C NMR, 19F NMR spectroscopy and CHN analysis. ► New compounds indicated potential bioactivities. ► Compounds resulting from incorporation of 4-amino-2-trifluoromethybenzonitrile are more active than those resulting from coupling with 4-aminobenzonitrile.