Synthesis and Anti-tumor Activity of Novel Glycyrrhetinic Acid Derivatives

Chemical Research in Chinese Universities ›› 2012, Vol. 28 ›› Issue (2): 214-219 .

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Synthesis and Anti-tumor Activity of Novel Glycyrrhetinic Acid Derivatives

MENG Yan-qiu¹, DING Jia-qi¹, LIU Yuan¹, NIE Hui-hui¹, GUAN Sai¹, ZOU Chao¹, ZHAO Na¹, CHEN Hong², CAO Bo²

1. Department of Pharmaceutical Engineering, Shenyang University of Chemical Technology, Shenyang 110142, P. R. China;
2. Department of Pharmacognosy, Medical College of Chinese People's Armed Police Forces, Tianjin 300162, P. R. China

Received:2011-09-26 Revised:2011-12-23 Online:2012-03-25 Published:2012-03-08
Contact: MENG Yan-qiu E-mail:mengyanqiu@hotmail.com
Supported by:
Supported by the Project-sponsored by Scientific Research Foundation for Returned Overseas Chinese Scholars, Ministry of Education of China(No.20080890) and the Key Project of Chinese University Science Research of Liaoning Educational Commission, China(No.L2010433).

Abstract

Abstract: Twenty-five derivatives of glycyrrhetinic acid(GA) modified on the A-ring, at C30 and C11 positions were synthesized. Their in vitro cytotoxicity against various cancer cell lines[henrietta lacks strain of cancer cells(HeLa), human hepatocellular liver carcinoma cells(HepG2) and human gastric carcinoma cells(BGC-823)] was evaluated by standard MTT[3-(4,5-dimethyl-2-thiazol-yl)-2,5-diphenyl-2H-tetrazolium bromide] assay. All the tested derivatives were found to have stronger cell growth inhibitory than their parent compound GA. Among them, compounds 3a, 5a, and 8d have similar activity on HeLa cell line, and compound 8a has similar activity on HeLa, HepG2 and BGC-823 cell lines as Gefitinib.

Key words: Glycyrrhetinic acid derivative, Anti-tumor activity, Structure modification

MENG Yan-qiu, DING Jia-qi, LIU Yuan, NIE Hui-hui, GUAN Sai, ZOU Chao, ZHAO Na, CHEN Hong, CAO Bo. Synthesis and Anti-tumor Activity of Novel Glycyrrhetinic Acid Derivatives[J]. Chemical Research in Chinese Universities, 2012, 28(2): 214-219 .

References

[1] Zhang W. J., Chen S. P., Lu X., Zhou G. C., Chem. J. Chinese Universities, 2010, 31(11), 2206 [2] Liu D., Meng Y. Q., Zhao J., Chen L. G., Chem. Res. Chinese Uni-versities, 2008, 24(1), 42 [3] Ohuchi K., Kamada Y., Levine L., Tsurufuji S., Prostaglandins. Med., 1981, 7, 457 [4] Finney R. S., Tarnoky A. L., J. Pharm. Pharmacol., 1960, 12, 49 [5] Pompei R., Flore O., Maccialis M. A., Pani A., Loddo B., Nature, 1979, 281, 689 [6] Park H. Y., Park S. H., Yoon H. K., Han M. J., Kim D. H., Arch. Pharm. Res., 2004, 27, 57 [7] Finney R. S. H., Somers G. F., J. Pharm. Pharmacol., 1958, 10, 613 [8] Tanaka S., Uno C., Akimoto M., Tabata M., Honda C., Kamisako W., Med., 1991, 57, 527 [9] Xu C. L., Ju Y., Gao Z. B., Hu J., Kang X., A Compound Named 3-Aryl-2-ene-glycyrrhetinic Acid with Antitumor Activity and Its Synthetic Methods, CN 102268061A, 2011 [10] Takizawa Haruo, Journal of Kyoto Pref. Univ. Med., 1985, 94(10), 999 [11] Luo H. L., Huang W., Zhang H. L., Wu Q. N., Huang M. S., Zhang D. F., Yang F. Y., Chinese-German Journal of Clinical Oncology, 2004, 3(3), 137 [12] Terasawa T., Okada T., Nishino H., Eur. J. Med. Chem., 1992, 27(4), 689 [13] Hu J., Wu Y., Zhao C. Y., Ju Y., Chem. J. Chinese Universities, 2010, 31(9), 1762 [14] Askam V., Baines C. M., Smith H. J., J. Pharmac., 1996, 18(3), 168 [15] Baran J. S., Langford D. D., Liang C. D., Pitzele B. S., J. Med. Chem., 1974, 17(2), 184 [16] Cai L. L., Synthesis, Anti-tumor Activities of Novel Ursolic Acid Analogues, Shenyang University of Chemical Technology, Shenyang, 2009 [17] Feng J. H., Synthesis of Oleanolic Acid, 18β-Glycyrrhetinic Acid and Ursolic Acid Derivatives and Primary Research on Their Cytotoxic Activities, Zhejiang University, Hangzhou, 2006 [18] Maruzen Pharmaceutical Co., Ltd., 11-Deoxyglycyrrhetic Acid, JP 58180455, 1982

Synthesis and Anti-tumor Activity of Novel Glycyrrhetinic Acid Derivatives

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