Citation: 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 shu

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

Huang Yanmin ^a ,
Qi Binbin ^a ,
Cui Jianguo ^a,b,*,, ,
Gan Chunfang ^a ,
Yang Chunhui ^a ,
Liu Chang ^a ,
Chen Shuang ^a ,
Shi Haixin ^b,*,,

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

Corresponding author: Cui Jianguo, cuijg1954@126.com Shi Haixin, shihaixin206@163.com
Received Date: 23 December 2015
Revised Date: 5 March 2016

Fund Project: the Guangxi Colleges and University Key Laboratory Foundation of Beibu Gulf Oil and Natural Gas Resoure Effective Utilization No. 2014KLOG09the National Natural Science Foundation of China No. 21462009

Figures(2)

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.
- cholesterol,
- heterosteroids,
- B-norcholesteryl thiazoles,
- antiproliferative activity
1. [1]
  Luigio, T.; Saverio, F.; Catia, G. Steroids 2002, 67, 687.
2. [2]
  Mohared, R. M.; Elmegged, G. A.; Abdel-Salam, O. M. E.; Doss, S. H.; William, M. G. Steroid 2011, 76, 1190.
3. [3]
  Natalija, M.; Krstić, N. M.; Mira, S.; Bjelaković, M. S.; Vladimir, D.; Pavlović, V. D. Steroids 2012, 77, 558.
4. [4]
  Mohared, R. M.; Al-Omran, F. Steroids 2012, 77, 1551.
5. [5]
  Festi, D.; Montagnani, M.; Azzaroli, F.; Lodato, F.; Mazzella, G.; Roda, A. Curr. Clin. Pharmacol 2007, 2(2), 155.
6. [6]
7. [7]
8. [8]
  Traf, D. T. P. Cancer Lett. 2006, 243, 202.
9. [9]
  John, W. B.; Brent, R. C.; Robert, A. K.; Murray, H. G. M.; Michèle, R. P. Nat. Prod. Rep. 2013, 30, 237.
10. [10]
  John, W. B.; Brent, R. C.; Robert, A. K.; Murray, H. G. M.; Michèle, R. P. Nat. Prod. Rep. 2014, 31, 160.
11. [11]
  John, W. B.; Brent, R. C.; Robert, A. K.; Murray, H. G. M.; Michèle, R. P. Nat. Prod. Rep. 2015, 32, 116.
12. [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. [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. [14]
  Wang, H. L.; Fang, J. M.; Cheng, Y. S. Phytochemistry 1998, 48, 1391.
15. [15]
  Miyamoto, T.; Kodama, K.; Aramaki, Y.; Higuchi, R.; Soest, R. W. M. Tetrahedron Lett. 2001, 42, 6349.
16. [16]
  Wei, X. M.; Rodriguez, A. D.; Wang, Y. H.; Franzblau, S. G. Tetrahedron Lett. 2007, 48, 8851.
17. [17]
  Wei, X. M.; Rodriguez, A. D.; Wang, Y. H.; Franzblau, S. G. Bioorg. Med. Chem. Lett. 2008, 18, 5448.
18. [18]
  Gan, C. F.; Fan, L. H.; Cui, J. G.; Huang, Y. M.; Jiao, Y. X.; Wei, W. X. Steroids 2012, 77, 1061.
19. [19]
  Gan, C. F.; Fan, L. H.; Huang, Y. M.; Liu, Z. P.; Cui, J. G. Med. Chem. 2013, 9, 846.
20. [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. [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. [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. [23]
24. [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. [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. [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. [27]
  Kovács, D.; Mótyán, G.; Wölfling, J.; Kovács, I.; Zupkó, I.; Frank, É. Bioorg. Med. Chem. Lett. 2014, 24, 1265.
28. [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. [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. [30]
  Lesyk, R.; Zimenkovsky, B.; Atamanyuk, D.; Jensen, F.; Kononowicz, K. K.; Gzella, A. Bioorg. Med. Chem. 2006, 14, 5230.
31. [31]
  Kashfi, K. Adv. Pharmacol. 2009, 57, 31.
32. [32]
  Ramla, M. M.; Omar, M. A.; El-Khamry, A. M.; El-Diwan, H. I. Bioorg. Med. Chem. 2006, 14, 7324.
33. [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. [34]
  Mohareb, R. M.; Al-Omran, F. Steroids 2012, 77, 1551.
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