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Chinese Journal of Organic Chemistry >

2016 , Vol. 36 >Issue 7: 1602 - 1610

DOI: https://doi.org/10.6023/cjoc201512031

Articles

Synthesis and Evaluation of Some New B-Norcholesteryl Thiazole Compounds as Anticancer Agents

  • Huang Yanmin ,
  • Qi Binbin ,
  • Cui Jianguo ,
  • Gan Chunfang ,
  • Yang Chunhui ,
  • Liu Chang ,
  • Chen Shuang ,
  • Shi Haixin
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  • a. College of Chemistry and Material Science, Guangxi Teachers Education University, Nanning 530001;
    b. Guangxi Colleges and University Key Laboratory of Beibu Gulf Oil and Natural Gas Resoure Effective Utilization, Qizhou University, Qizhou

Received date: 2015-12-23

  Revised date: 2016-03-05

  Online published: 2016-03-25

Supported by

Project supported by the National Natural Science Foundation of China (No. 21462009) and the Guangxi Colleges and University Key Laboratory Foundation of Beibu Gulf Oil and Natural Gas Resoure Effective Utilization (No. 2014KLOG09).

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Abstract

Some B-norcholesteryl thiazole compounds were synthesized and their structures were determined by IR, NMR and HRMS. The antiproliferative activity of the compounds against human lung carcinoma (A549), cervical carcinoma (HeLa), liver carcinoma (HEPG2) and normal kidney epithelial (HEK293T) cells was assayed. The results showed that some compounds with a structure of N-methylthiazole showed distinct antiproliferative activity against A549 and HEPG2 cells. The compounds with a structure of N-phenylthiazole displayed a selective antiproliferative activity against HeLa cells and were almost inactive to HEK293T cells. The research provided a theoretical reference for the exploration of new anti-cancer agents.

Key words： cholesterol; heterosteroids; B-norcholesteryl thiazoles; antiproliferative activity

Cite this article

Huang Yanmin , Qi Binbin , Cui Jianguo , Gan Chunfang , Yang Chunhui , Liu Chang , Chen Shuang , Shi Haixin . Synthesis and Evaluation of Some New B-Norcholesteryl Thiazole Compounds as Anticancer Agents[J]. Chinese Journal of Organic Chemistry, 2016 , 36(7) : 1602 -1610 . DOI: 10.6023/cjoc201512031

References

[1] Luigio, T.; Saverio, F.; Catia, G. Steroids 2002, 67, 687.
[2] Mohared, R. M.; Elmegged, G. A.; Abdel-Salam, O. M. E.; Doss, S. H.; William, M. G. Steroid 2011, 76, 1190.
[3] Natalija, M.; Krsti?, N. M.; Mira, S.; Bjelakovi?, M. S.; Vladimir, D.; Pavlovi?, V. D. Steroids 2012, 77, 558.
[4] Mohared, R. M.; Al-Omran, F. Steroids 2012, 77, 1551.
[5] Festi, D.; Montagnani, M.; Azzaroli, F.; Lodato, F.; Mazzella, G.; Roda, A. Curr. Clin. Pharmacol 2007, 2(2), 155.
[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] Zhang, X.-J.; Cui, J.-G.; Li, Y.; Chen, S.-J. Chin. J. Org. Chem. 2010, 30, 655 (in Chinese). (张晓佳, 崔建国, 李莹, 陈思静, 有机化学, 2010, 30, 655.)
[8] Traf, D. T. P. Cancer Lett. 2006, 243, 202.
[9] John, W. B.; Brent, R. C.; Robert, A. K.; Murray, H. G. M.; Michèle, R. P. Nat. Prod. Rep. 2013, 30, 237.
[10] John, W. B.; Brent, R. C.; Robert, A. K.; Murray, H. G. M.; Michèle, R. P. Nat. Prod. Rep. 2014, 31, 160.
[11] John, W. B.; Brent, R. C.; Robert, A. K.; Murray, H. G. M.; Michèle, R. P. Nat. Prod. Rep. 2015, 32, 116.
[12] Jorge, A. R. S.; João, F. S. C.; Marco, A. C. N.; Samuel, M. S.; Alcino, J. L.; Manuel, C. S.; Luisa, S. M. Nat. Prod. Rep. 2013, 30, 324.
[13] Wentworth, P.; Nieva, J.; Takeuchi, C.; Galve, R.; Wentworth, A. D.; Dilley, R. B.; DeLaria, G. A.; Saven, A.; Babior, B. M.; Janda, K. D.; Eschenmoser, A.; Lerner, R. A. Science 2003, 302, 1053.
[14] Wang, H. L.; Fang, J. M.; Cheng, Y. S. Phytochemistry 1998, 48, 1391.
[15] Miyamoto, T.; Kodama, K.; Aramaki, Y.; Higuchi, R.; Soest, R. W. M. Tetrahedron Lett. 2001, 42, 6349.
[16] Wei, X. M.; Rodriguez, A. D.; Wang, Y. H.; Franzblau, S. G. Tetrahedron Lett. 2007, 48, 8851.
[17] Wei, X. M.; Rodriguez, A. D.; Wang, Y. H.; Franzblau, S. G. Bioorg. Med. Chem. Lett. 2008, 18, 5448.
[18] Gan, C. F.; Fan, L. H.; Cui, J. G.; Huang, Y. M.; Jiao, Y. X.; Wei, W. X. Steroids 2012, 77, 1061.
[19] Gan, C. F.; Fan, L. H.; Huang, Y. M.; Liu, Z. P.; Cui, J. G. Med. Chem. 2013, 9, 846.
[20] Gan, C. F.; Lin, Q. F.; Cui, J. G.; Feng, J, D.; Guo, J. N.; Liao, H. Y.; Huang, Y. M. Steroids 2014, 79, 37.
[21] Singh, H.; Kapoor, V. K.; Paul, D. In Progress in Medicinal Chemistry, Vol. 16, Eds.: Ellis, G. P.; West, G. B., Springer, Amsterdam, 1979, pp. 35~150.
[22] Singh, H.; Jindal, D. P.; Yadav, M. R.; Kumar, M. In Progress in Medicinal Chemistry, Vol. 28, Eds.: Ellis, G. P.; West, G. B., Elsevier Science Publishers, Amsterdam, 1991, pp. 233~300.
[23] Cui, J. G.; Liu, L.; Gan, C. F.; Xiao, Q.; Huang, Y. M. Prog. Chem. 2014, 26(2/3), 320 (in Chinese). (崔建国, 刘亮, 甘春芳, 肖琦, 黄燕敏, 化学进展, 2014, 26(2/3), 320.)
[24] 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.
[25] Guo, H.; Zhang, G. L.; 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.
[26] Huang, L. H.; Zheng, Y. F.; Lu, Y. Z.; Song, C. J.; Wang, Y. G.; Yu, B.; Liu, H. M. Steroids 2012, 77, 710.
[27] Kovács, D.; Mótyán, G.; Wölfling, J.; Kovács, I.; Zupkó, I.; Frank, É. Bioorg. Med. Chem. Lett. 2014, 24, 1265.
[28] Zhang, B. L.; Zhang, E.; Pang, L. P.; Song, L. X.; Li, Y. F.; Yu, B.; Liu, H. M. Steroids 2013, 78, 1200.
[29] Cui, J. G.; Qi, B. B.; Gan, C. F.; Liu, Z. P.; Huang, H.; Lin, Q. F.; Zhao, D. D.; Huang, Y. M. Mar. Drugs 2015, 13, 2488.
[30] Lesyk, R.; Zimenkovsky, B.; Atamanyuk, D.; Jensen, F.; Kononowicz, K. K.; Gzella, A. Bioorg. Med. Chem. 2006, 14, 5230.
[31] Kashfi, K. Adv. Pharmacol. 2009, 57, 31.
[32] Ramla, M. M.; Omar, M. A.; El-Khamry, A. M.; El-Diwan, H. I. Bioorg. Med. Chem. 2006, 14, 7324.
[33] Sun, L. P.; Jiang, Z.; Gao, L. X.; Liu, X. F.; Quan, Y. C.; Zheng, G. H.; Li, J.; Piao, H. Chin. J. Org. Chem. 2013, 33, 1496.
[34] Mohareb, R. M.; Al-Omran, F. Steroids 2012, 77, 1551.

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