[KSCI] Korea Science Citation Index Service

http://dx.doi.org/10.5012/bkcs.2010.31.12.3684

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

Gan, Lin-Ling (Laboratory of Bioorganic & Medicinal Chemistry, School of Chemistry and Chemical Engineering, Southwest University)
Fang, Bo (Laboratory of Bioorganic & Medicinal Chemistry, School of Chemistry and Chemical Engineering, Southwest University)
Zhou, Cheng-He (Laboratory of Bioorganic & Medicinal Chemistry, School of Chemistry and Chemical Engineering, Southwest University)

Publication Information

Bulletin of the Korean Chemical Society / v.31, no.12, 2010 , pp. 3684-3692 More about this Journal

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 $25\;{\mu}g/mL$ , 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: $25\;{\mu}g/mL$ , $50\;{\mu}g/mL$ and $100\;{\mu}g/mL$ 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.

Keywords

Piperazine; Imidazole; Antibacterial; Antifungal; Cytotoxicity;

Citations & Related Records

Times Cited By KSCI : 1 (Citation Analysis)
Times Cited By Web Of Science : 11 (Related Records In Web of Science)
Times Cited By SCOPUS : 11

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1	/ Acta Crystallographica Section E: Structure Reports Online
2	/ Bioorganic and Medicinal Chemistry Letters
3	/ Acta Crystallographica Section E: Structure Reports Online
4	/ Kao Teng Hsueh Hsiao Hua Heush Hsueh Pao/ Chemical Journal of Chinese Universities
5	/ European Journal of Medicinal Chemistry