A new class of 2-(4-cyanophenyl amino)-4-(6-bromo-4-quinolinyloxy)-6-piperazinyl (piperidinyl)-1,3,5-triazine analogues with antimicrobial/antimycobacterial activity

Abstract

This study presents the synthesis and in vitro pharmacological evaluations of novel 2-(4-cyanophenyl amino)-4-(6-bromo-4-quinolinyloxy)-6-piperazinyl (piperidinyl)-1,3,5-triazines. The title compounds were assayed for their in vitro antimicrobial activity against eight bacteria (Staphylococcus aureus, Bacillus cereus, Escherichia coli, Pseudomonas aeruginosa, Klebsiella pneumoniae, Salmonella typhi, Proteus vulgaris, Shigella flexneria) and four fungi (Aspergillus niger, Aspergillus fumigatus, Aspergillus clavatus, Candida albicans) using paper disc diffusion and agar streak dilution method as well as against Mycobacterium tuberculosis H37Rv strain using BACTEC MGIT and Lowenstein-Jensen MIC method. The bioassay results indicate that nine compounds namely 5d, 5h, 5n, 5p, 5q, 5r, 5s, 5t and 5u could be considered as possible potential agents with dual antimicrobial and antimycobacterial activities. The structures of the compounds were elucidated with the aid of IR, ¹H NMR, ¹³C NMR, ¹⁹F NMR spectroscopy and CHN analysis.

Keywords::

• 2,4,6-trichloro-1,3,5-triazin
• 6-bromo-4-hydroxyquinoline
• piperazine
• antimicrobial activity
• antimycobacterial activity

Acknowledgments

The authors are thankful to Applied Chemistry Department of S. V. National Institute of Technology, Surat for the scholarship, encouragement and facilities. The authors wish to offer their deep gratitude to Microcare Laboratory, Surat, India for carrying out the biological screenings and Centre of Excellence, Vapi, India for carrying out ¹H NMR, ¹³C NMR and ¹⁹F NMR analysis.

Declaration of interest

The authors report no conflict of interest.

Supplementary material

Detailed discussion on the analytical and biological characterization is included within the supplementary information. Tables containing zone of inhibition and MICs for all the newly synthesized compounds are included within the supplementary information.