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

Synthesis of Dehydroepiandrosteronyl Thiazole Derivatives and Their Antiproliferative Evaluation

Cui Jianguo ^a,b ,
Zhao Dandan ^a ,
He Dongmei ^a ,
Huang Yanmin ^a ,
Liu Zhiping ^a ,
Lin Qifu Shi ^b ,
Haixin Gan ^b ,
^a,,

1.
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;
2.
b Guangxi Colleges and University Key Laboratory of Beibu Gulf Oil and Natural Gas Resoure Effective Utilization, Qizhou University, Qinzhou 535000

Corresponding author: ,
Received Date: 18 September 2015
Available Online: 18 November 2015
Fund Project: 国家自然科学基金(Nos. 21462009, 21562007) (Nos. 21462009, 21562007)广西高校北部湾石油天然气资源有效利用重点实验室开放课题(No. 2014KLOG09) (No. 2014KLOG09)

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.
- dehydroepiandrosterone,
- thiazole,
- dehydroepiandrosteronyl thiazole derivatives,
- antiproliferative activity
1. [1]
  [1] Bansal, R.; Acharya, P. C. Chem. Rev. 2014, 114, 6986.
2. [2]
  [2] Mohared, R. M.; Elmegged, G. A.; Abdel-Salam, O. M. E.; Doss, S. H.; William, M. G. Steroids 2011, 76, 1190.
3. [3]
  [3] Krstić, N. M.; Bjelaković, M. S.; Pavlović, V. D.; Robeyns, K.; Juranić, Z. D.; Matić, I.; Novaković, I.; Sladić, D. M. Steroids 2012, 77, 558.
4. [4]
  [4] Mohared, R. M.; Al-Omran, F. Steroids 2012, 77, 1551.
5. [5]
  [5] Frank, E.; Schneider, G. J. Steroid Biochem. Mol. Biol. 2013, 127, 301.
6. [6]
  [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. [7]
  [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. [8]
  [8] Traf, D. T. P. Cancer Lett. 2006, 243, 202.
9. [9]
  [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. [10]
  [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. [11]
  [11] Lesyk, R.; Zimenkovsky, B.; Atamanyuk, D.; Jensen, F.; Kononowicz, K. K.; Gzella, A. Bioorg. Med. Chem. 2006, 14, 5230.
12. [12]
  [12] Kashfi, K. Adv. Pharmacol. 2009, 57, 31.
13. [13]
  [13] Ramla, M. M.; Omar, M. A.; El-Khamry, A. M.; El-Diwan, H. I. Bioorg. Med. Chem. 2006, 14, 7324.
14. [14]
  [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. [15]
  [15] Mohareb, R. M.; Al-Omran, F. Steroids 2012, 77, 1551.
16. [16]
  [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. [17]
  [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. [18]
  [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. [19]
  [19] Cui, J.; Qi, B.; Gan, C.; Liu, Z.; Huang, H.; Lin, Q.; Zhao, D.; Huang. Y. Mar. Drugs 2015, 13, 2488.
20. [20]
  [20] Cui, J.; Liu, L.; Zhao, D.; Gan, C.; Huang, X.; Xiao, Q.; Qi, B.; Yang, L.; Huang, Y. Steroids 2015, 95, 32.
21. [21]
  [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. [22]
  [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. [23]
  [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. [24]
  [24] Ahluwalia, V. K.; Chibber, S. S.; Goyal, B. Indian J. Chem., Sect. B 1996, 35, 856.
25. [25]
  [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.)
1. [1]
  Jing WU , Puzhen HUI , Huilin ZHENG , Pingchuan YUAN , Chunfei WANG , Hui WANG , Xiaoxia GU . Synthesis, crystal structures, and antitumor activities of transition metal complexes incorporating a naphthol-aldehyde Schiff base ligand. Chinese Journal of Inorganic Chemistry, 2024, 40(12): 2422-2428. doi: 10.11862/CJIC.20240278
2. [2]
  Ping Song , Nan Zhang , Jie Wang , Rui Yan , Zhiqiang Wang , Yingxue Jin . Experimental Teaching Design on Synthesis and Antitumor Activity Study of Cu-Pyropheophorbide-a Methyl Ester. University Chemistry, 2024, 39(6): 278-286. doi: 10.3866/PKU.DXHX202310087
3. [3]
  Xiaotong LU , Pan ZHANG , Zijie ZHAO , Lei HUANG , Hongwei ZUO , Lili LIANG . Antitumor and antibacterial activities of pyridyl Schiff base indium and dysprosium complexes. Chinese Journal of Inorganic Chemistry, 2025, 41(8): 1523-1532. doi: 10.11862/CJIC.20250073
4. [4]
  Yue Zhao , Yanfei Li , Tao Xiong . Copper Hydride-Catalyzed Nucleophilic Additions of Unsaturated Hydrocarbons to Aldehydes and Ketones. University Chemistry, 2024, 39(4): 280-285. doi: 10.3866/PKU.DXHX202309001
5. [5]
  Zhuoming Liang , Ming Chen , Zhiwen Zheng , Kai Chen . Multidimensional Studies on Ketone-Enol Tautomerism of 1,3-Diketones By ¹H NMR. University Chemistry, 2024, 39(7): 361-367. doi: 10.3866/PKU.DXHX202311029
6. [6]
  Yihui Song , Shangshang Qin , Kai Wu , Chengyun Jin , Bin Yu . 生物化学在高水平创新型药学人才培养中的交叉融合应用——以去甲基化酶LSD1抑制剂的活性评价为例. University Chemistry, 2025, 40(6): 341-352. doi: 10.12461/PKU.DXHX202406018
7. [7]
  Jiahao Zeng , Hui Chao . 诱导程序性细胞死亡的金属抗肿瘤药物研究. University Chemistry, 2025, 40(6): 145-159. doi: 10.12461/PKU.DXHX202406019
8. [8]
  Jian Li , Yu Zhang , Rongrong Yan , Kaiyuan Sun , Xiaoqing Liu , Zishang Liang , Yinan Jiao , Hui Bu , Xin Chen , Jinjin Zhao , Jianlin Shi . Highly Efficient, Targeted, and Traceable Perovskite Nanocrystals for Photoelectrocatalytic Oncotherapy. Acta Physico-Chimica Sinica, 2025, 41(5): 100042-0. doi: 10.1016/j.actphy.2024.100042
9. [9]
  Hanxue LIU , Shijie LI , Meng REN , Xuling XUE , Hongke LIU . Design and antitumor properties of dehydroabietic acid functionalized cyclometalated iridium(Ⅲ) complex. Chinese Journal of Inorganic Chemistry, 2025, 41(8): 1483-1494. doi: 10.11862/CJIC.20250031
10. [10]
  Yurong Tang , Yunren Shi , Yi Xu , Bo Qin , Yanqin Xu , Yunfei Cai . Innovative Experiment and Course Transformation Practice of Visible-Light-Mediated Photocatalytic Synthesis of Isoquinolinone. University Chemistry, 2024, 39(5): 296-306. doi: 10.3866/PKU.DXHX202311087
11. [11]
  Lihui Jiang , Wanrong Dong , Hua Yang , Yongqing Xia , Hongjian Peng , Jun Yuan , Xiaoqian Hu , Zihan Zeng , Yingping Zou , Yiming Luo . Study on Extraction of p-Hydroxyacetophenone. University Chemistry, 2024, 39(11): 259-268. doi: 10.12461/PKU.DXHX202402056
12. [12]
  Guoze Yan , Bin Zuo , Shaoqing Liu , Tao Wang , Ruoyu Wang , Jinyang Bao , Zhongzhou Zhao , Feifei Chu , Zhengtong Li , Yamauchi Yusuke , Melhi Saad , Xingtao Xu . Opportunities and Challenges of Capacitive Deionization for Uranium Extraction from Seawater. Acta Physico-Chimica Sinica, 2025, 41(4): 2404006-0. doi: 10.3866/PKU.WHXB202404006
13. [13]
  Jianfeng Yan , Yating Xiao , Xin Zuo , Caixia Lin , Yaofeng Yuan . Comprehensive Chemistry Experimental Design of Ferrocenylphenyl Derivatives. University Chemistry, 2024, 39(4): 329-337. doi: 10.3866/PKU.DXHX202310005
14. [14]
  Siran Wang , Yinuo Wang , Yilong Zhao , Dazhen Xu . Advances in the Application and Preparation of Rhodanine and Its Derivatives. University Chemistry, 2025, 40(5): 318-327. doi: 10.12461/PKU.DXHX202407033
15. [15]
  Linjie ZHU , Xufeng LIU . Synthesis, characterization and electrocatalytic hydrogen evolution of two di-iron complexes containing a phosphine ligand with a pendant amine. Chinese Journal of Inorganic Chemistry, 2025, 41(5): 939-947. doi: 10.11862/CJIC.20240416
16. [16]
  Jianan Hong , Chenyu Xu , Yan Liu , Changqi Li , Menglin Wang , Yanwei Zhang . Decoding the interfacial competition between hydrogen evolution and CO₂ reduction via edge-active-site modulation in photothermal catalysis. Acta Physico-Chimica Sinica, 2025, 41(9): 100099-0. doi: 10.1016/j.actphy.2025.100099
17. [17]
  Jia-He Li , Yu-Ze Liu , Jia-Hui Ma , Qing-Xiao Tong , Jian-Ji Zhong , Jing-Xin Jian . 洛芬碱衍生物的合成、化学发光与重金属离子检测. University Chemistry, 2025, 40(6): 230-237. doi: 10.12461/PKU.DXHX202407080
18. [18]
  Liangzhen Hu , Li Ni , Ziyi Liu , Xiaohui Zhang , Bo Qin , Yan Xiong . A Green Chemistry Experiment on Electrochemical Synthesis of Benzophenone. University Chemistry, 2024, 39(6): 350-356. doi: 10.3866/PKU.DXHX202312001
19. [19]
  Guojie Xu , Fang Yu , Yunxia Wang , Meng Sun . Introduction to Metal-Catalyzed β-Carbon Elimination Reaction of Cyclopropenones. University Chemistry, 2024, 39(8): 169-173. doi: 10.3866/PKU.DXHX202401060
20. [20]
  Xuan Zhou , Yi Fan , Zhuoqi Jiang , Zhipeng Li , Guowen Yuan , Laiying Zhang , Xu Hou . Liquid Gating Mechanism and Basic Properties Characterization: a New Experimental Design for Interface and Surface Properties in the Chemistry “101 Plan”. University Chemistry, 2024, 39(10): 113-120. doi: 10.12461/PKU.DXHX202407111

Get Citation

PDF

XML

Metrics

PDF Downloads(0)
Abstract views(1422)
HTML views(127)

通讯作者: 陈斌, bchen63@163.com

1.
沈阳化工大学材料科学与工程学院沈阳 110142