Synthesis and Biological Evaluation of Novel Benzimidazole Derivatives Bearing a Heterocyclic Ring at 4/5 Position

다국어 초록 (Multilingual Abstract)

A series of novel benzimidazole derivatives bearing a heterocyclic ring as oxadiazole (21-32), thiadiazole (33- 34), triazole (35-36) were synthesized and evaluated for their activities against Coxsackie virus B3 and B6 in Vero cells. Compounds 21-26, 31-36 with moieties of 2'-pyridyl, 3'-pyridyl and 4'-pyridyl at the 2-position and oxadiazoles, thiadiazole, or triazole substituent at the 4- or 5-position generally displayed activities against CVB3 and CVB6. Especially compound 24 (IC50 = 1.08 μg/mL, SI = 61.7 against CVB3) was the promising candidate as lead compound for anti-enteroviral drug. It was observed in the incorporation of heterocyclic rings in benzimidazole at the 5-position could enhance their biological activities.

참고문헌 (Reference)

1 Barker, H. A., 235 : 480-, 1960

2 Reed, L. J., 27 : 493-, 1938

3 Mavrova, A., 41 : 1412-, 2006

4 Kohara, Y., 5228-, 1996

5 Mederski, W. W., 14 : 3763-, 2004

6 Richards, M. L., 47 : 6451-, 2004

7 Elmer, G. I., 117 : 23-, 1995

8 Mader, M., 18 : 179-, 2008

9 Arjmand, F., 40 : 1103-, 2005

10 Chien, T. C., 47 : 5743-, 2004

11 Valdez, J., 12 : 2221-, 2002

12 Kus, C., 16 : 4294-, 2008

13 Kuhler, T. C., 41 : 1777-, 1998

14 El-Emam, A. A., 12 : 5107-, 2004

15 Kucukguzel, S. G., 37 : 197-, 2002

16 Kagthara, P. R., 38B : 572-, 1999

17 Akhter, M., 44 : 2372-, 2009

18 Unangast, P. C., 35 : 3691-, 1992

19 Khan, M. S. Y., 11 : 119-, 2001

20 O’Neal, J. B., 5 : 617-, 1962

21 Luo, Y. P., 15 : 1716-, 2007

22 Hiroshi, K., 18 : 60-, 1970

23 Prasad, D. J., 44 : 551-, 2009

24 Walczak, K., 39 : 849-, 2004

25 Holla, B. S., 38 : 759-, 2003

26 Amir, M., 39 : 535-, 2004

27 Almasirad, A., 14 : 6057-, 2004

28 Merkle, I., 76 : 9900-, 2002

29 Xue, F., 19 : 2641-, 2011

30 Gilbert, B. E., 30 : 201-, 1986

31 Hemming, K., "1,2,4-Oxadiazoles, In Comprehensive Heterocyclic Chemistry III" Elsevier 243-, 2008