Synthesis and biological evaluation of novel s-triazine based aryl/heteroaryl entities: Design, rationale and comparative study

Abstract

The urgent need in search of new biological entities to fight back with recent drugresistant microbial flora, has led us report a library of s-triazine derivatives. The intermediate 4-((4-chloro-6-methoxy-1,3,5-triazin-2-yl)amino)benzonitrile 3 was substituted with various thiophenol, phenol, aniline and piperazine/piperidine/morpholine moieties to furnish the final 35 target compounds i.e. (4a–j), (5a–j), (6a–g) and (7a–h), respectively. These compounds were screened for in vitro antibacterial evaluation against bacteria (Staphylococcus aureus MTCC 96, Bacillus cereus MTCC 619, Escherichia coli MTCC 739, and Pseudomonas aeruginosa MTCC 741) and antifungal activity against fungi (Candida albicans MTCC 183, Aspergillus niger MTCC 282, and Aspergillus clavatus MTCC 1323). The title compounds were further subjected for antituberculosis activity against Mycobacterium tuberculosis H37Rv strain using the BACTEC MGIT method. In this biological evaluation, thiophenol derivatives were found to be more active than the rest (i.e. –Thiophenol >-piperazine > -Aniline > -phenol). The final compounds were characterized by FT-IR, 1H NMR, 13C NMR, mass spectroscopy and elemental analysis.