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A series of novel diphenylpiperazine 1,2,3-triazole derivatives were designed, synthesized and characterized by proton nuclear magnetic resonance, carbon-13 nuclear magnetic resonance, infrared and mass spectroscopy. The prepared compounds were investigated in vitro for antibacterial, antifungal and cytotoxic activities. Preliminary results showed that nitroimidazole piperazine 14b was active against bacteria Bacillus subtilis, Micrococcus luteus, Bacillus proteus, Escherichia coli and B. typhi with MIC values of 25 μg/ml, but showed moderate activity against Candida albicans and Saccharomyces cerevisiae (MIC- 50 μg/ml). Moreover, the 1,2,3-triazole-linked nitroimidazole piperazine compound 15b and benzimidazole piperazine 15e were found to be effective in vitro against the PC-3 cell line and the cell survival rates were only 67 and 60 %, respectively at a concentration of 100 μM in a dose-dependent manner. Further, molecular docking experiments suggested that the nitro and hydroxyl groups of compound 14b could insert into base-pairs of DNA hexamer duplex by the formation of hydrogen bonds with guanine of DNA.

Design, Synthesis and Relational Biological Evaluation of Novel Diphenylpiperazine 1,2,3-triazole Derivatives