Synthesis characterization and biological evaluation of pyridine benzimidazole thiazole and 1 3 5 triazine containing and related novel organic molecules

Abstract

A series of new chlorinated thiabendazoles (6a m) have been synthesized from readily available anilines (1a-d) and 4-cyanothiazole in moderate to good yields. All synthesized compounds were fully characterized using IR, 1H NMR, 13C NMR, and mass spectrometry. Additionally, the structure of the compound (6f) was confirmed by single-crystal X-ray diffraction. In addition, synthesis of 2-substituted benzimidazoles and 2-phenyl benzothiazole was investigated using our optimized conditions and the outcome is presented herein. All the chlorinated thiabendazoles (6a m) were assessed for their activity against bacteria and fungi such as S. aureus, E. coli, K. pneumoniae, A. baumannii, and P. aeruginosa, C. albicans and C. neoformans. newlineThe six-membered, symmetric heterocycle 1,3,5-triazine and its derivatives have fascinated reasonable devotion as due to the proven powerful bioactive antibacterial, antifungal, antiviral, and antineoplastic agents, etc. A series of 1,3,5-triazine derivatives (3a-o) were synthesized by a single step reaction and characterized by 1H NMR, 13C NMR, and mass spectroscopic analysis. Antimicrobial screening of title compounds (3a-o) was examined against five bacterial and two fungal strains. In vitro study revealed that the freshly synthesized 6-(thiazol-4-yl)-1,3,5-triazine-2,4-diamine (3o) showed good antibacterial growth inhibition against Escherichia coli, Klebsiella pneumoniae and Acinetobacter baumannii bacterial strains, and even the fungi Cryptococcus neoformans. Molecular docking studies were performed on the X-ray crystal structure of Escherichia coli 24 kDa domain in complex with Clorobiocin (PDB code: 1KZN; resolution 2.30 Å) using Surflex-Dock program of Sybyl-X software. The results obtained are very encouraging. newline newline