研究论文

3-羟基-6-腙及6-羰基-3-腙胆甾烷的合成及抗肿瘤活性评估

  • 崔建国 ,
  • 刘畅 ,
  • 刘亮 ,
  • 甘春芳 ,
  • 卢艳 ,
  • 陈爽 ,
  • 董新 ,
  • 黄燕敏
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  • a 北部湾环境演变与资源利用教育部重点实验室 广西师范学院化学与材料科学学院 南宁 530001;
    b 四川万之药业股份有限公司 成都 610041;
    c 广西防城港市高级中学 防城港 538001

收稿日期: 2016-04-04

  修回日期: 2016-06-17

  网络出版日期: 2016-08-12

基金资助

国家自然科学基金(Nos. 21562007,21462009)、广西高校科学研究(No. KY2015D077)及有机化学广西高校重点学科资助项目.

Synthesis and Antitumor Activities of Cholestane Derivatives with a Structure of 3-Hydroxy-6-hydrazone or 6-Carbonyl-3-hydrazone

  • Cui Jianguo ,
  • Liu Chang ,
  • Liu Liang ,
  • Gan Chunfang ,
  • Lu Yan ,
  • Chen Shuang ,
  • Dong Xin ,
  • Huang Yanmin
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  • a Key Laboratory of Beibu Gulf Environmental Change and Resources Utilization of Ministry of Education, College of Chemistry and Material Science, Guangxi Teachers Education University, Nanning 530001;
    b Sichuan Welltz Pharm Inc., Chengdu 610041;
    c Fangchenggan High School, Fangchenggang 538001

Received date: 2016-04-04

  Revised date: 2016-06-17

  Online published: 2016-08-12

Supported by

Project supported by the National Natural Science Foundation of China (Nos. 21562007, 21462009), the Science Research Project of Guangxi Teachers University (No. KY2015D077) and the Organic Chemistry in Guangxi University Key Disciplines.

摘要

以胆甾醇为原料,通过不同的合成方法,制备得到8个新的具有3-羟基-6-腙及3个6-羰基-3-腙结构的胆甾烷腙衍生物,所有合成化合物都通过了IR,NMR及HRMS的结构表征.另外,采用人肝癌细胞(Bel-7404)及胃癌细胞(SGC-7901)对合成化合物的抗肿瘤活性进行了研究,结果表明所合成的3-羟基-6-腙胆甾烷衍生物对所测试的肿瘤细胞株表现出明显的生长增殖抑制活性,本研究结果为甾体抗肿瘤药物的合成研究提供了有用的参考.

本文引用格式

崔建国 , 刘畅 , 刘亮 , 甘春芳 , 卢艳 , 陈爽 , 董新 , 黄燕敏 . 3-羟基-6-腙及6-羰基-3-腙胆甾烷的合成及抗肿瘤活性评估[J]. 有机化学, 2016 , 36(12) : 2933 -2940 . DOI: 10.6023/cjoc201604007

Abstract

Some cholestane hydrazone derivatives with a structure of 3-or 6-hydrazone group were synthesized by different chemical methods using cholesterol as a starting material, and their structures were characterized by IR, NMR and HRMS. The antiproliferative activity of the compounds in vitro was evaluated against human Bel-7404 and SGC-7901 cancer cells. The results showed that the cholestane derivatives with the structure of 3-hydroxy-6-hydrazone exhibited distinct cytotoxicity. The information obtained from the studies is valuable for the design of novel steroidal chemotherapeutic drugs.

参考文献

[1] Cui, J.-G; Huang, Y.-M.; Gan, C.-F. Modern Steroid Chemistry, Science Press, Beijing, 2014, pp. 67~230(in Chinese).(崔建国, 黄燕敏, 甘春芳, 现代甾体化学, 科学出版社, 北京, 2014, pp. 67~230.)
[2] Cui, J.-G.; Liu, L.; Gan, C.-F.; Xiao, Q.; Huang, Y.-M. Prog. Chem. 2014, 26, 320(in Chinese).(崔建国, 刘亮, 甘春芳, 肖琦, 黄燕敏, 化学进展, 2014, 26, 320.)
[3] Attard, G.; Reid, A. H. M.; Yap, T. A.; Raynaud, F.; Dowsett, M.; Barrett, M.; Settatree, S.; Parker, C.; Martins, V.; Folkerd, E.; Clark, J.; Cooper, C. S. J. Clin. Oncol. 2008, 26, 4563.
[4] Ma, B.; Xiao, Z. Y.; Chen, Y. J.; Lei, M.; Meng, Y.-H.; Guo, D.-A.; Liu, X.; Hu, L.-H. Steroids 2013, 78, 508.
[5] Guo, H.; Zhang, G.; Zhang, T.; He, X.-R.; Wu, Z.-Y.; Xiao, Y.-L.; Pan, Y.-H.; Qiu, G.-F.; Liu, P.; Hu, X.-M. Eur. J. Med. Chem. 2011, 46, 3662.
[6] Huang, L.-H.; Zheng, Y.-F.; Lu, Y.-Z.; Song, C.-J.; Wang, Y.-G.; Yu, B.; Liu, H.-M. Steroids 2012, 77, 710.
[7] Kovács, D.; Mótyán, G.; Wölfling, J.; Kovács, I.; Zupkó, I.; Frank, É. Bioorg. Med. Chem. Lett. 2014, 24, 1265.
[8] Zhang, B.-L.; Zhang, E.; Pang, L.-P.; Song, L.-X.; Li, Y.-F.; Yu, B.; Liu, H.-M. Steroids 2013, 78, 1200.
[9] Cui, J. G.; Fan, L.; Huang, L. L.; Liu, H. L.; Zhou, A. M. Steroids 2009, 74, 62.
[10] Cui, J.-G.; Wang, H.; Huang, Y.-M.; Xin, Y.; Zhou, A.-M. Ster-oids 2009, 74, 1057.
[11] Cui, J.-G.; Fan, L.; Huang, Y.-M.; Xin, Y.; Zhou, A.-M. Steroids 2009, 74, 989
[12] Huang, Y.-M.; Cui, J.-G.; Li, Y.; Fan, L.; Jiao, Y.-M.; Su, S.-Y. Med. Chem. Res. 2013, 22, 409.
[13] Huang, Y.-M.; Su, S.-Y.; Jia, L.-Y.; Gan, C.-F.; Kong, E.-B.; Cui, J.-G. Chin. J. Org. Chem. 2014, 34, 1816(in Chinese).(黄燕敏, 苏绍烊, 贾琳怡, 甘春芳, 林啟福, 孔二斌, 崔建国, 有机化学, 2014, 34, 1816.)
[14] Huang, Y.-M.; Yao, Q.-C.; Liu, Z. P.; Gan, C.-F.; Zheng, J.-H.; Sheng, H.-B.; Shi, H.-X.; Cui, J.-G. Chin. J. Org. Chem. 2015, 35, 2168(in Chinese).(黄燕敏, 姚秋翠, 刘志平, 甘春芳, 郑嘉桦, 盛海兵, 石海信, 崔建国, 有机化学, 2015, 35, 2168.)
[15] Gan, C.-F.; Cui, J.-G.; Su, S.-Y.; Lin, Q.-F.; Jia, L.-Y.; Fan, L.-H.; Huang, Y.-M. Steroids 2014, 87, 99.
[16] Huang, Y.-M.; Cui, J.-G.; Zeng, Q.-X.; Zeng, C.; Chen, Q.; Zhou, A.-M. Steroids 2012, 77, 829.
[17] Cui, J.-G.; Liu, L.; Zhao, D.-D.; Gan, C.-F.; Huang, X.; Xiao, Q.; Qi, B.-B.; Yang, L.; Huang, Y.-M. Steroids 2015, 95, 32.
[18] Cui, J.-G.; Zeng, L.-M.; Su, J. Y. Chem. J. Chin. Univ. 2003, 24, 639(in Chinese).(崔建国, 曾陇梅, 苏镜娱, 高等学校化学学报, 2003, 24, 639.)

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