Synthesis of Azole-containing Piperazine Derivatives and Evaluation of their Antibacterial, Antifungal and Cytotoxic Activities

Abstract

A series of azole-containing piperazine derivatives have been designed and synthesized. The obtained compounds were investigated in vitro for their antibacterial, antifungal and cytotoxic activities. The preliminary results showed that most compounds exhibited moderate to significant antibacterial and antifungal activities in vitro. 1-(4-((4-chlorophenyl) (phenyl)methyl)piperazin-1-yl)-2-(1H-imidazol-1-yl)ethanone and 1-(4-((4-Chlorophenyl)(phenyl)methyl)piperazin-1-yl)-2-(2-phenyl-1H-imidazol-1-yl)ethanone gave remarkable and broad-spectrum antimicrobial efficacy against all tested strains with MIC values ranging from 3.1 to 25 μg/mL, and exhibited comparable activities to the standard drugs chloramphenicol and fluconazole in clinic. Moreover, 2-((4-((4-chlorophenyl)(phenyl)methyl)piperazin-1-yl)methyl)-1H-benzo [d]imidazole was found to be the most effective in vitro against the PC-3 cell line, reaching growth inhibition values (36.4, 60.1 and 76.5%) for each tested concentration: 25 μM, 50 μΜ and 100 μM in dose-dependent manner. The results also showed that the azole ring had noticeable effect on their antimicrobial and cytotoxic activities, and imidazole and benzimidazole moiety were much more favourable to biological activity than 1,2,4-triazole.

3-Nitrotriazole-based piperazides as potent antitrypanosomal agents

“…Piperazide-based compounds demonstrate a broad range of biological activities including, but not limited to, antibacterial, antiparasitic, antifungal, anthelmintic and antitubercular activity [29][30][31][32][33]. In particular, some metronidazole-bearing piperazides exhibit appreciable antigiardial and/or antitrichomonal activity [31].…”

A new silver(I) coordination polymer containing 3-methylthio-(1H)-1,2,4-triazole as precursor for preparation of silver nanorods

“…The chemistry of 1,2,4-triazole and its derivatives has received considerable attention due to their wide potential in the treatment of various diseases as antibacterial, antifungal, antitumor, anti-inflammatory, hypotensive, hypothermic and other medicinal drugs [1][2][3][4][5][6][7][8]. In addition to these applications, 1,2,4-triazole and its derivatives have been widely investigated as ligands by the fact that they unite the coordination geometry of both pyrazoles and imidazoles and exhibit versatile coordination modes upon ligation to metals [9].…”

Synthesis and anticancer activity evaluation of N-[4-(2-methylthiazol-4-yl)phenyl]acetamide derivatives containing (benz)azole moiety

“…Several studies including the anticancer activity of certain thiazole analogs were reported by medicinal chemists [13][14][15][16][17][18][19][20] . In addition to thiazoles, some other azole compounds have also attracted much attention due to their prominent utilization as antitumor agents 21 . For instance, derivatives of triazole 22 , imidazole 23 , benzimidazole 24,25 , benzoxazole [26][27][28] and benzothiazole 29 have shown anticancer properties.…”