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

다국어 초록 (Multilingual 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.

참고문헌 (Reference)

1 Sojakova, M., 157 : 163-169, 2004

2 Chai, X. Y., 44 : 1913-1920, 2009

3 Phillips O. A., 43 : 1095-1104, 2008

4 Lyman, C. A., 44 : 9-35, 1992

5 McCalmont, W. F., 14 : 3691-3695, 2004

6 Gan, L. L., 30 : 127-131, 2009

7 Cai, J. L., 34 : 454-462, 2009

8 Gan, L. L., 44 : 1361-1368, 2009

9 Foroumadi, A., 42 : 985-992, 2007

10 Lohray, B. B., 16 : 1557-1561, 2006

11 Foroumadi, A, 16 : 3499-3503, 2006

12 Watkins, W. J., 17 : 2802-2806, 2007

13 Upadhayaya, R. S., 12 : 2225-2238, 2004

14 Rokosz, L. L., 15 : 5537-5543, 2005

15 Chen, J. J., 14 : 6539-6547, 2006

16 Shami, P. J., 49 : 4356-4366, 2006

17 Mayence, A., 39 : 547-553, 2004

18 Cunico, W., 44 : 1363-1368, 2009

19 Smits, R. A., 51 : 2457-2467, 2008

20 Penjišević, J., 340 : 456-465, 2007

21 Becker, O. M., 49 : 3116-3135, 2006

22 Bean, D. C., 63 : 349-352, 2009

23 Coban, A. Y., 43 : 457-461, 2009

24 Chaudhary, P., 14 : 1819-1826, 2006

25 Farzaliev, V. M., 82 : 928-930, 2009

26 Weiderhold, K. N., 118 : 1032-1040, 2006

27 Senthilkumar, P., 16 : 2558-2569, 2008

28 Narendra Sharath Chandra, J. N., 14 : 6621-6627, 2006

29 Ananda Kumar, C. S., 44 : 1223-1229, 2009

30 Huang, S. L., 17 : 1243-1245, 2007

31 Bellina, F., 16 : 5757-5762, 2006

32 Wu, J., 46 : 404-409, 2007

33 Güven, Ö. Ö., 17 : 2233-2236, 2007

34 Mi, J. L., 23 : 84-86, 2008

35 Zhou, C. H., 333 : 313-326, 2001

36 Cai, J. L., 18 : 598-608, 2009

37 Luo, Y., 342 : 386-393, 2009

38 Zhang, F. F., 20 : 1881-1884, 2010

39 Hamied, Y. K., 2001

40 Press, J. B., 1989

41 Press, J. B., 35 : 4509-4515, 1992

42 Wright, H. B., 11 : 390-391, 1968

43 Foye, W. O., "ples of Medicinal Chemistry, 4th ed" Williams and Wilkins 1995

44 Fang-Kui Ren, "Synthesis and Antibacterial Activity of 1,3-Diallyltrisulfane Derivatives" 대한화학회 30 (30): 687-690, 2009