Articles

Synthesis and Anti-inflammatory Activity of Novel Benzimidazole (Benzothiazole) Phenylursolate

  • LI Cai-Hu ,
  • YANG Cong-Ling ,
  • ZHANG Kuan ,
  • SHI Wan-Qi ,
  • LI Jian-Zhong ,
  • LI Ying ,
  • YIN Shu-Fan
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  • a Faculty of Chemistry Sichuan University, Chengdu 610064;
    b College of Chemical and Material Science, Sichuan Normal University, Chengdu 610066;
    c Sichuan Guokang Pharmaceutical Co., Ltd, Chengdu 610041

Received date: 2011-04-01

  Revised date: 2011-08-03

  Online published: 2011-09-09

Abstract

A novel series of the benzimidazole or benzothiazole phenyl ester derivatives of ursolic acid 4a4h were prepared via ursolic acid, substituted benzaldehyde, and o-phenylendiamine or 2-aminothiophenol. The compounds were structurally confirmed by 1H NMR, IR and HRMS techniques. The preliminary bioassay test demonstrated that compounds 4d and 4g had potent anti-inflammatory activity.

Cite this article

LI Cai-Hu , YANG Cong-Ling , ZHANG Kuan , SHI Wan-Qi , LI Jian-Zhong , LI Ying , YIN Shu-Fan . Synthesis and Anti-inflammatory Activity of Novel Benzimidazole (Benzothiazole) Phenylursolate[J]. Chinese Journal of Organic Chemistry, 2012 , 32(01) : 133 -137 . DOI: 10.6023/cjoc1104011

References

[1] (a) Baricevic, D.; Sosa, S.; Della, R.; Tubaro, A.; Simonovska, B.; Krosna, A. J. Ethnopharmacol. 2001, 75, 125. (b) Liu, J. J. Ethnopharmacol. 1995, 49, 57.

[2] Yang, D.-J.; Li, Y.; Yin, S.-F. Chin. J. Org. Chem. 2008, 28, 1055 (in Chinese). (杨定菊, 李颖, 尹述凡, 有机化学, 2008, 28, 1055.)

[3] Ma, C.-M.; Cai, S.-Q.; Cui, J.-R.; Wang, R.-Q.; Tu, P.-F.; Hattori, M. Eur. J. Med. Chem. 2005, 40, 582.

[4] Tatsuzaki, J.; Taniguchi, M.; Bastow, K. F.; Nakagawa-Goto, K.; Morris-Natschke, S. L.; Itokawa, H. Bioorg. Med. Chem. 2007, 15, 6193.

[5] Huang, M. T.; Ho, C. T.; Wang, Z. Y.; Ferraro, T.; Lou, Y. R.; Stauber, K. Cancer Res. 1994, 54, 701.

[6] Saraswat, B.; Vises, P. K.; Agarwa, D. P. Phytother. Res. 2000, 14, 163.

[7] Gromovaya, V. F.; Shapoval, G. S.; Luik, A. I.; Averkov, A. I.; Lozinskii, M. O. Russ. J. Gen. Chem. 1997, 67(6), 942.

[8] Craigo, W. A.; Lesueur, B. W.; Skibo, E. B. J. Med. Chem. 1999, 42(17), 3324.

[9] Wells, G.; Bradshaw, T. D.; Diana, P.; Seaton, A.; Shi, D.-F.; Westwell, A. D.; Stevens, M. F. G. Bioorg. Med. Chem. Lett. 2000, 10, 513.

[10] Rana, A.; Siddiqui, N.; Khan, S. A. Indian J. Pharm. Sci. 2007, 69, 10.

[11] Chen, L.; Zhang, Y.-H.; Bi, X.-L.; Luo, Y.-Q. Central South Pharm. 2006, 12, 416 (in Chinese). (陈莉, 奕华, 毕小玲, 罗叶青, 中南药学, 2006, 12, 416.)

[12] Parish, R. C.; Stock, L. M. Tetrahedron Lett. 1964, 5(20), 1285.

[13] Yang, H.-J.; Hu, C.; Li, Y.; Yin, S.-F. Chin. J. Org. Chem. 2008, 28, 899 (in Chinese). (杨鸿均, 胡翠, 李颖, 尹述凡, 有机化学, 2008, 28, 899.)

[14] Kenny, R. S.; Mashelkar, U. C. J. Heterocycl. Chem. 2006, 43, 1367.

[15] Cramer, F.; Bär, H. P.; Rhaese, H. J.; Sänger, W.; Scheit, K. H.; Schneider, G.; Tennigkeit, J. Tetrahedron Lett. 1963, 4(16), 1039.
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