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Chinese Journal of Organic Chemistry >

2016 , Vol. 36 >Issue 3: 630 - 637

DOI: https://doi.org/10.6023/cjoc201509021

Notes

Synthesis of Dehydroepiandrosteronyl Thiazole Derivatives and Their Antiproliferative Evaluation

  • Cui Jianguo ,
  • Zhao Dandan ,
  • He Dongmei ,
  • Huang Yanmin ,
  • Liu Zhiping ,
  • Lin Qifu ,
  • Shi Haixin ,
  • Gan Chunfang
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  • a Key Laboratory of Environment Change and Resources Use in Beibu Gulf Ministry of Education, Chemistry and Materials Science College, 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, Qinzhou 535000

Received date: 2015-09-18

  Revised date: 2015-11-18

  Online published: 2015-11-26

Supported by

Project supported by the National Natural Science Foundation of China (Nos. 21462009, 21562007), the Key Laboratory Project of Effective Utilization of Petroleum and Natural Gas Resources in Guangxi Beibu Gulf (No. 2014KLOG09), and the Synthetic and Natural Functional Molecular Chemistry Lab of Guangxi.

Fold

Abstract

Using dehydroepiandrosterone as starting material, 16 dehydroepiandrosteronyl thiazol derivatives with different structures had been synthesized via microwave irradiation assisted one-pot reaction and general synthetic method, and their structures were characterized by IR, NMR and HRMS. The antiproliferative activity of the compounds was evaluated against human cervical carcinoma (HeLa), human lung carcinoma (A549), human liver carcinoma cells (HEPG2) and normal kidney epithelial cells (HEK293T). The results showed that compound 4 displayed significant inhibitory activity to tested cancer cells, and the values of IC50 were 13.2, 11.3 and 8.3 μmol·L-1 respectively, but was almost inactive to HEK293T cells (IC50>100 μmol·L-1). However, other compounds did not exhibit distinct antiproliferative activity to all tested cells.

Key words： dehydroepiandrosterone; thiazole; dehydroepiandrosteronyl thiazole derivatives; antiproliferative activity

Cite this article

Cui Jianguo , Zhao Dandan , He Dongmei , Huang Yanmin , Liu Zhiping , Lin Qifu , Shi Haixin , Gan Chunfang . Synthesis of Dehydroepiandrosteronyl Thiazole Derivatives and Their Antiproliferative Evaluation[J]. Chinese Journal of Organic Chemistry, 2016 , 36(3) : 630 -637 . DOI: 10.6023/cjoc201509021

References

[1] Bansal, R.; Acharya, P. C. Chem. Rev. 2014, 114, 6986.
[2] Mohared, R. M.; Elmegged, G. A.; Abdel-Salam, O. M. E.; Doss, S. H.; William, M. G. Steroids 2011, 76, 1190.
[3] Krsti?, N. M.; Bjelakovi?, M. S.; Pavlovi?, V. D.; Robeyns, K.; Jurani?, Z. D.; Mati?, I.; Novakovi?, I.; Sladi?, D. M. Steroids 2012, 77, 558.
[4] Mohared, R. M.; Al-Omran, F. Steroids 2012, 77, 1551.
[5] Frank, E.; Schneider, G. J. Steroid Biochem. Mol. Biol. 2013, 127, 301.
[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] Cui, J.-G.; Liu, L.; Gan, C.-F.; Xiao, Q. 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.)
[10] Cui, S.-F.; Wang, Y.; Lü, J.-S.; Damu Guri, L. V. ; Zhou, C.-H. Sci. China, Ser B 2012, 42, 1105 (in Chinese). (崔胜峰, 王艳, 吕敬松, Damu Guri, L. V.; 周成合, 中国科学, 化学, 2012, 42, 1105.)
[11] Lesyk, R.; Zimenkovsky, B.; Atamanyuk, D.; Jensen, F.; Kononowicz, K. K.; Gzella, A. Bioorg. Med. Chem. 2006, 14, 5230.
[12] Kashfi, K. Adv. Pharmacol. 2009, 57, 31.
[13] Ramla, M. M.; Omar, M. A.; El-Khamry, A. M.; El-Diwan, H. I. Bioorg. Med. Chem. 2006, 14, 7324.
[14] 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 (in Chinese). (孙良鹏, 姜哲, 高立信, 刘晓芳, 全迎春, 郑光浩, 李佳, 朴虎日, 有机化学, 2013, 33, 1496.)
[15] Mohareb, R. M.; Al-Omran, F. Steroids 2012, 77, 1551.
[16] Yuan, M.-Y.; Liu, M.; Zhang, Y.-Q.; Yan, H.-F.; Li, D.-F.; Zhang, D. N.; Liu, H. M. Chin. J. Org. Chem. 2012, 32, 1746 (in Chinese). (袁明月, 刘敏, 张英群, 闫红飞, 李德富, 张冬暖, 刘卉闵, 有机化学, 2012, 32, 1746.)
[17] Chen, C.-J.; Song, B. A. Pesticide 2005, 44(2), 53 (in Chinese). (陈才俊, 宋宝安, 农药, 2005, 44(2), 53.)
[18] Shingate, B. B.; Hazra, B. G.; Salunke, D. B.; Pore, V. S.; Shirazi, F.; Deshpande, M. V. Eur. J. Med. Chem. 2011, 46, 3681.
[19] Cui, J.; Qi, B.; Gan, C.; Liu, Z.; Huang, H.; Lin, Q.; Zhao, D.; Huang. Y. Mar. Drugs 2015, 13, 2488.
[20] Cui, J.; Liu, L.; Zhao, D.; Gan, C.; Huang, X.; Xiao, Q.; Qi, B.; Yang, L.; Huang, Y. Steroids 2015, 95, 32.
[21] Zhao, D.-D.; Qi, B.-B.; Yang, L.; Huang, Y.-M.; Gan, C.-F.; Cui, J.-G. Chin. J. Med. Chem. 2014, 24, 470 (in Chinese). (赵丹丹, 戚斌斌, 杨雷, 黄燕敏, 甘春芳, 崔建国, 中国药物化学杂志, 2014, 24, 470.)
[22] Qi, B.-B.; Liu, L.; Zhao, D.-D; Yang, L.; Huang, Y. M.; Cui, J.-G. Chem. Res. Appl. 2015, 27, 665 (in Chinese). (戚斌斌, 刘亮, 赵丹丹, 杨雷, 甘春芳, 黄燕敏, 崔建国, 化学研究与应用, 2015, 27, 665.)
[23] Yang, S.; Fu, Z.-D.; Han, R. Acta Pharm. Sinica 2001, 36, 576 (in Chinese). (杨笋, 付招娣, 韩锐, 药学学报, 2001, 36, 576.)
[24] Ahluwalia, V. K.; Chibber, S. S.; Goyal, B. Indian J. Chem., Sect. B 1996, 35, 856.
[25] Yuan, M.-Y.; Liu, W. H.; Zhang, Y. Q.; Yan, H. F.; Zhang, D.-N.; Liu, H.-M.; Wang, J.-P. Chin. J. Org. Chem. 2013, 33, 1108 (in Chinese). (袁明月, 刘伟华, 张英群, 闫红飞, 张冬暖, 刘卉闵, 王建平, 有机化学, 2013, 33, 1108.)

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