Synthesis, biological evaluation and docking studies of a new series of tris-heterocycles containing pyrazole, triazole and oxadiazole

摘要

A new series of 3-aryl/hetaryl-6-(5-methyl-1-phenyl-1H-pyrazol-4-yl)-[1,2,4]triazolo[3,4-b][1,3,4]oxadiazoles 7a-j have been synthesized, characterized by spectral means, and evaluated for their antimicrobial and antioxidant properties. Amongst the screened compounds 7a-j, the triazole moiety bearing electron-withdrawing group on the 4~(th) position of phenyl viz. 4-chlorophenyl 7c, 4-nitrophenyl 7f and 2,4-difluorophenyl 7h exhibit excellent antibacterial activity towards all the tested bacteria viz. Staphylococcus aureus, Bacillus licheniformis, Pseudomonas aeruginosa and Escherichia coli. On the other hand, triazole moiety bearing electron-donating group on the 4~(th) position of phenyl viz. 4-hydroxyphenyl 7d, 4-methoxy-phenyl 7e and 4-aminophenyl 7g show prominent antifungal activity towards the tested fungi viz. Candida albicans and Fusarium oxysporum. These results are supported by molecular docking studies and through binding interactions as well. Antioxidant studies reveal that the compounds in which the triazole moiety bearing phenyl 7a, 4-methoxyphenyl 7e, 2,4-difluorophenyl 7h and 3-pyridyl 7j is present on the 4~(th) position, display significant antioxidant properties. In brief, most of the newly synthesized compounds have emerged as potential antimicrobial and antioxidant agents for further development.