Chinese Journal of Organic Chemistry >
Synthesis and Antiproliferative Evaluation of Chenodeoxycholic Acid Containing-Nitrogen Derivatives
Received date: 2015-03-29
Revised date: 2015-05-23
Online published: 2015-06-19
Supported by
Project supported by the National Natural Science Foundation of China (Nos. 21462009, 21562007) and the Opening Project of Guangxi Colleges and Universities Key Laboratory of Beibu Gulf Oil and Natural Gas Resource Effective Utilization (No. 2014KLOG09).
Chenodeoxycholic acid nitrogen-containing derivatives display anti-tumor activities and induce apoptosis of the cacer cells. Some chenodeoxycholic acid derivatives possessing various nitrogen-containing substituent in 3-or 7-position of steroidal nucleus were designed and synthesized using chenodeoxycholic acid as starting materials. Their structures were characterized by IR, NMR and MS. Antiproliferative activities of the compounds were assayed against human gastric cancer cells (SGC-7901), human hepatic cancer (Bel-7404) and prostate cancer cell (PC-3) by MTT method. The results showed that some nitrogen-containing derivatives of chenodeoxycholic acid had better antiproliferative activities against Bel-7404 and PC-3 cells.
Huang Yanmin , Yao Qiucui , Liu Zhiping , Gan Chunfang , Zheng Jiahua , Sheng Haibing , Shi Haishing , Cui Jianguo . Synthesis and Antiproliferative Evaluation of Chenodeoxycholic Acid Containing-Nitrogen Derivatives[J]. Chinese Journal of Organic Chemistry, 2015 , 35(10) : 2168 -2175 . DOI: 10.6023/cjoc201503048
[1] Richard, J. P.; Olga, K. W. Evidence-Based Completmentary Altern. Med. 2005, 2(1), 49.
[2] Dimitrios, T. P. T.; George, D. G.; Catherine, K.; Athanasios, P.; Panayiotis, K.; Charalambos, C. Breast Cancer Res. Treat. 2006, 97, 17.
[3] Dimitrios, T. P. T. Cancer Lett. 2006, 243, 202.
[4] 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, 化学进展, 2014, 26, 320.)
[5] Huang, Y.-M.; Cui, J.-G.; Gan, C.-F.; Yao, Q.-C.; Jia, L.-Y. Prog. Chem. 2012, 24, 61 (in Chinese). (黄燕敏, 崔建国, 甘春芳, 姚秋翠, 贾琳怡, 化学进展, 2012, 24, 61.)
[6] Chen, S.-J.; Cui, J.-G.; Li, Y.; Fan, L.-H. Chin. J. Org. Chem. 2011, 31, 187 (in Chinese). (陈思静、崔建国、李莹、范良华, 有机化学, 2011, 31, 187.)
[7] Cui, J. G.; Fan, L.; Huang, L. L.; Liu, H. L.; Zhou, A. M. Steroids 2009, 74, 62.
[8] Cui, J. G.; Fan, L.; Huang, Y. M.; Xin, Y.; Zhou, A. M. Steroids 2009, 74, 989.
[9] Huang, Y. M.; Cui, J. G.; Chen, S. J.; Gan, C. F.; Zhou, A. M. Steroids 2011, 76, 1346.
[10] Huang, Y. M.; Cui, J. G.; Chen, S. J.; Gan, C. F.; Yao, Q. C.; Lin, Q.-F. Bioorg. Med. Chem. Lett. 2013, 23, 2265.
[11] Huang, Y. M.; Cui, J. G.; Chen, S. J.; Lin, Q. F.; Song, H. C.; Gan, C. F.; Su, B.; Zhou, A. M. Mar. Drugs 2014, 12, 1715.
[12] 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.
[13] Im, E. O.; Choi, Y. H.; Paik, K. J.; Suh, H.; Jin, Y.; Yoo, Y. H.; Kim, N. D. Cancer Lett. 2001, 163, 83.
[14] Im, E. O.; Choi, S. H.; Suh, H.; Choi, Y. H.; Yoo, Y. H.; Kim, N. D. Cancer Lett. 2005, 229, 49.
[15] Sharma, R.; Majer, F.; Peta, V. K.; Wang, J.; Keaveney, R.; Kelleher, D.; Long, A.; Gilmer, J. F. Bioorg. Med. Chem. 2010, 18, 6886.
[16] Becker, S.; Reinehr, R.; Graf, D.; Dahl, S.; Häussinger, D. Cell Physiol. Biochem. 2007, 19, 89.
[17] Qin, C. Y.; Liu, H. Chin. J. Digestion 2007, 27, 124 (in Chinese). (秦成勇, 刘慧, 中华消化杂志, 2007, 27, 124.)
[18] Huang, Y. M.; Yao, Q. C.; Cui, J. G.; Gan, C. F.; Huang, Q. Y.; Su, B.; Zhou, A. M. Chem. Res. Chin. Univ. 2014, 30, 605.
[19] 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.
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