SIOC 中文
CJOG
Adv search

Chinese Journal of Organic Chemistry >

2018 , Vol. 38 >Issue 4: 919 - 925

DOI: https://doi.org/10.6023/cjoc201711016

Articles

Study on the Synthesis and Bioactivity of Diosgenin Antitumor Derivatives

  • Luo Zhuoma ,
  • Hu Yuegao ,
  • Wang Luhong ,
  • Yin Xiangjian ,
  • Ma Xiaodong ,
  • Yang Hongjun ,
  • Zhao Zhigang
Expand
  • a College of Chemistry and Environmental Protection Engineering, Southwest University for Nationalities, Chengdu 610041;
    b College of Pharmacy, Dalian Medical University, Dalian 116044;
    c Sichuan Chuanda Huaxi Pharmaceutical Co., Ltd., Chengdu 610014

Received date: 2017-11-08

  Revised date: 2018-01-05

  Online published: 2018-01-18

Supported by

Project supported by the National Natural Science Foundation of China (No. 21602083), the Southwest University for Nationalities Graduate Student Innovative Project (No. CX2016SZ045), and the Sichuan Provincial Department of Education Research Project (No. 15ZB0487).

Fold

Abstract

Nine novel diosgenin derivatives were designed and synthesized by using diosgenin as a precursor. Their structures were identified by 1H NMR, 13C NMR, IR and HRMS. Antitumor activity (A549, A431, H1975, HCT-116, Aspc-1, Ramos) and cytotoxicity (HBE, LO-2) were measured for all derivatives using thiazolyl blue tetrazolium bromide (MTT). The results show that most diosgenin derivatives have significant anti-tumor activity and low cytotoxicity.

Key words： diosgenin; derivative; antitumor activity; amide

Cite this article

Luo Zhuoma , Hu Yuegao , Wang Luhong , Yin Xiangjian , Ma Xiaodong , Yang Hongjun , Zhao Zhigang . Study on the Synthesis and Bioactivity of Diosgenin Antitumor Derivatives[J]. Chinese Journal of Organic Chemistry, 2018 , 38(4) : 919 -925 . DOI: 10.6023/cjoc201711016

References

[1] Tang, S. R.; Yang, R. T.; Pan, F. S. J. Plant. Resour. Environ. 2007, 16, 64(in Chinese). (唐世荣, 杨如同, 潘福生, 植物资源与环境学报, 2007, 16, 64.)
[2] Sun, Q.; Ju, Y.; Zhao, Y. F. Chin. Tradit. Herb. Drugs 2002, 33, 276(in Chinese). (孙麒, 巨勇, 赵玉芬, 中草药, 2002, 33, 276.)
[3] Mattew, J. K.; Mary, L. T.; Jing, Z. H. Bioorg. Med. Chem. 2008, 16, 3209.
[4] Liu, C.; Wang, Z. Z.; Zheng, W. West China J. Pharm. Sci. 2009, 24, 483(in Chinese). (刘超, 王珍珍, 郑微, 华西药学杂志, 2009, 24, 483.)
[5] Yue, L.; Chen, L.; Kou, J. P. Chin. J. Clin. Pharmacol. Ther. 2010, 15, 233(in Chinese). (岳蕾, 陈玲, 寇俊萍, 中国临床药理学与治疗学, 2010, 15, 233.)
[6] Zeng, C. L.; Gen, Q.; Wu, Y. K. West China J. Pharm. Sci. 2011, 26, 423(in Chinese). (曾春玲, 耿倩, 吴亚克, 华西药学杂志, 2011, 26, 423.)
[7] Wang, B.; Chun, J.; Liu, Y. Org. Biomol. Chem. 2012, 10, 8822.
[8] Wang, Y.; Pan, K.; Chang, T. J. Nat. Prod. 2011, 74, 580.
[9] Yayoi, T.; Naoko, K.; Akinori, H. Steroids 2009, 74, 504.
[10] Wang, L. J.; Wang, Y.; Chen, S. W. China J. Chin. Mater. Med. 2002, 27, 777(in Chinese). (王丽娟, 王岩, 陈声武, 中国中药杂志, 2002, 27, 777.)
[11] Cecile, C.; Bertrand, L. Cell Res. 2004, 14, 188.
[12] Huo, R.; Zhou, Q. L.; Wang, B. X. Acta Pharmacol. Sin. 2004, 25, 1077.
[13] Fu, W. W.; Wu, Y, K.; Fan, J. Z. West China J. Pharm. Sci. 2010, 25, 658(in Chinese). (傅微微, 吴亚克, 范举正, 华西药学杂志, 2010, 25, 658.)
[14] Liao, P. F.; Dong, J. H.; Fan, J. Z. West China J. Pharm. Sci. 2013, 28, 364(in Chinese). (廖鹏飞, 董江红, 范举正, 华西药学杂志, 2013, 28, 364.)
[15] Wu, Y. K.; He, G.; Fu, W. W. West China J. Pharm. Sci. 2012, 27, 22(in Chinese). (吴亚克, 何谷, 傅微微, 华西药学杂志, 2012, 27, 22.)
[16] Dong, J. H.; He, G.; Wu, Y. K. Chin. Pharmacol. Bull. 2012, 47, 1407(in Chinese). (董江红, 何谷, 吴亚克, 中国药学杂志, 2012, 47, 1407.)
[17] Zhang, H. B.; Yang, X. D.; Qin, C.; Liu, Y. L.; Li, L.; Liu, J. P. CN 1876672, 2006.
[18] Zhang, R.; Guo, X. R.; He, Y.; Huang, W. West China J. Pharm. Sci. 2013, 28, 229(in Chinese). (张瑞, 郭秀蓉, 何杨, 黄文, 华西药学杂志, 2013, 28, 229.)
[19] Ding, X. Y.; He, G.; Jiang, H. P. West China J. Pharm. Sci. 2012, 46, 539(in Chinese). (丁晓勇, 何谷, 蒋红平, 药学学报, 2012, 46, 539.)
[20] Geng, Q.; Zeng, C. L.; Fu, W. W. West China J. Pharm. Sci. 2009, 24, 475(in Chinese). (耿倩, 曾春玲, 傅微微, 华西药学杂志, 2009, 24, 475.)
[21] Lu, L. H.; Wu, D. S.; Peng, L. F.; Xu, M.; Lu, X. P.; Mei, S. X. J. Yunnan Univ. (Nat. Sci. Ed.) 2015, 37, 415(in Chinese). (陆礼和, 吴德松, 彭玲芳, 徐明, 陆雪萍, 梅双喜, 云南大学学报(自然科学版), 2015, 37, 415.)
[22] Zheng, W.; Jiang, H. P.; Wu, Y. K. West China J. Pharm. Sci. 2011, 26, 107(in Chinese). (郑微, 蒋红平, 吴亚克, 华西药学杂志, 2011, 26, 107.)
[23] Fu, X. L.; Han, Y. M.; Zhang, S. J. Drugs Clin. 2011, 26, 46(in Chinese). (付晓丽, 韩英梅, 张士俊, 现代药物与临床, 2011, 26, 46.)
[24] Fan, L. H.; Cui, J. G.; Gan, C. F.; Su, S. Y. Chem. Res. Appl. 2012, 24, 8(in Chinese). (范良华, 崔建国, 甘春芳, 苏绍烊, 化学研究与应用, 2012, 24, 8.)
[25] Fujii, N.; Mallari, J. P.; Hansell, E. J. Bioorg. Med. Chem. Lett. 2005, 15, 121.
[26] Renard, D.; Perruchon, J.; Giera, M. Bioorg. Med. Chem. 2009, 17, 8123.
[27] Stulov, S. V.; Zavialova, M. G.; Mehtiev, A. R. Bioorg. Med. Chem. Lett. 2010, 20, 5495.
[28] Handratta, V. D.; Vasaitis, T. S.; Njar, V. C. O. J. Med. Chem. 2005, 48, 2972.
[29] Banday, A. H.; Mir, B. P.; Lone, I. H. Steroids 2010, 75, 805.
[30] Xie, W. G.; Peng, H. R.; Zalkow, L. H. Bioorg. Med. Chem. 2000, 8, 699.
[31] Burbiel, J.; Bracher, F. Steroids 2003, 68, 587.
[32] Lian, P.; Li, L. L.; Geng, C. R.; Zhen, X. C.; Fu, W. J. Chem. Inf. Model. 2015, 55, 1616.
[33] Wang, Q. Q. M.S. Thesis, Anhui Medical University, Hefei, 2016(in Chinese). (王欠欠, 硕士论文, 安徽医科大学, 合肥, 2016.)
[34] Ai, Y. S.; Liu, L. Q.; Xu, C. H.; Chen, H. T.; Sun, X. X. Her. Med. 2015, 24, 626(in Chinese). (艾又生, 刘力强, 徐楚鸿, 陈华庭, 孙小香, 医药导报, 2015, 24, 626.)

Options
Outlines

/

〈 〉