Citation: Huang Yanmin, Pang Chunling, Yang Chunhui, Zhan Junyan, Gan Chunfang, Pang Liping, Liu Xiaolan, Cui Jianguo. Synthesis and Evaluation of Some New Aza-A-homocholesteryl-lactam Thiazole Derivatives as Anticancer Agents[J]. Chinese Journal of Organic Chemistry, ;2018, 38(6): 1484-1492. doi: 10.6023/cjoc201710005 shu

Synthesis and Evaluation of Some New Aza-A-homocholesteryl-lactam Thiazole Derivatives as Anticancer Agents

College of Chemistry and Material Science, Guangxi Teachers Education University, Nanning 530001

Corresponding author: Cui Jianguo, cuijg1954@126.com
Received Date: 8 October 2017
Revised Date: 13 December 2017
Available Online: 6 June 2018
Fund Project: the Guangxi Colleges and University Key Laboratory Foundation of Beibu Gulf Oil and Natural Gas Resource Effective Utilization 2014KLOG09Project supported by the National Natural Science Foundation of China (Nos. 21462009, 21562007), the Technology and Development Project of Nanning City (No. 20171125-5), the Guangxi Colleges and University Key Laboratory Foundation of Beibu Gulf Oil and Natural Gas Resource Effective Utilization (No. 2014KLOG09)the National Natural Science Foundation of China 21562007the Technology and Development Project of Nanning City 20171125-5the National Natural Science Foundation of China 21462009

Figures(3)

Using a testosterone as a raw material, a steroidal skelecton with A-homo-lactam was constructed. Then, some new aza-A-homocholesteryl-lactam thiazole derivatives were synthesized by modifying of the 17-hydroxyl and introducing of various heterocycles, and their structures were determined by IR, NMR and HRMS. The antiproliferative activity of the compounds against different carcinoma cells was assayed. The results show that some compounds display a distinct antiproliferative activity against tested cancer cells and are almost inactive to HEK293T cells.
- testosterone,
- heterosteroids,
- aza-A-homocholesteryl-lactam thiazole derivatives,
- antiproliferative activity
1. [1]
  Festi, D.; Montagnani, M.; Azzaroli, F.; Lodato, F.; Mazzella, G.; Roda, A.; Di-Biase, A. R; Roda, E.; Simoni, P.; Colecchia, A. Curr.Clin.Pharmacol. 2007, 2, 155. doi: 10.2174/157488407780598171
2. [2]
  Ifere, G.; Barr, E.; Equan, A.; Gordon, K.; Singh, U. P.; Chaudhary, J.; Igietseme, J. U.; Ananaba, G. A. Cancer Detect. Prev. 2009, 32, 319. doi: 10.1016/j.cdp.2008.12.002
3. [3]
  Morzycki, J. W. Steroids 2014, 83, 62. doi: 10.1016/j.steroids.2014.02.001
4. [4]
  João, F. S.; Carvalho, M.; Manuel, C. S.; João, N.; Moreira, S. S.; Melo, M. L. S. J.Med. Chem. 2011, 54, 6375. doi: 10.1021/jm200803d
5. [5]
  Jorge, A. R.; Salvador, J. F. S.; Carvalho, Marco A. C.; Neves, S. M.; Silvestre, A. J.; Leitão, M.; Manuel C. S. Nat. Prod.Rep. 2013, 30, 324. doi: 10.1039/C2NP20082A
6. [6]
  Ranju, B.; Pratap, C. A. Chem. Rev. 2014, 114, 6986. doi: 10.1021/cr4002935
7. [7]
  Liun, Q.-F.; Cui, J.-G.; Gan, C.-F. Chin. J.Org.Chem. 2012, 32, 2214(in Chinese).
8. [8]
  Huang, Y. M.; Cui, J. G.; Zhong, Z. G.; Gan, C. F.; Zhang, W. Y.; Song, H. C. Bioorg.Med.Chem.Lett. 2011, 21, 3641. doi: 10.1016/j.bmcl.2011.04.093
9. [9]
  Huang, Y. M.; Cui, J. G.; Chen, S. J.; Gan, C. F.; Zhou, A. M. Steroids 2011, 76, 1346. doi: 10.1016/j.steroids.2011.06.013
10. [10]
  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. doi: 10.3390/md12041715
11. [11]
  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. doi: 10.1016/j.bmcl.2012.08.064
12. [12]
  Cui, S. F.; Wang, Y.; Lv, J. S.; Damu Guri L. V.; Zhou C. H. Sci. China Chem. 2012, 42, 1105(in Chinese).
13. [13]
  Kashfi, K. Adv. Pharmacol. 2009, 57, 31. doi: 10.1016/S1054-3589(08)57002-5
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. doi: 10.6023/cjoc201212012
15. [15]
  Mohareb, R. M.; Al-Omran, F. Steroids 2012, 77, 1551. doi: 10.1016/j.steroids.2012.09.007
16. [16]
  Cui, J. G.; Liu, L.; Gan, C. F.; Xiao, Q.; Huang, Y. M. Prog. Chem. 2014, 26, 320(in Chinese).
17. [17]
  Cui, J. G.; Zhao, D. D.; He, D. M.; Huang, Y. M.; Liu, Z. P.; Liu, X. F.; Shi, H. X.; Gan, C. F. Chin. J. Org. Chem. 2016, 36, 630(in Chinese).
18. [18]
  Huang, Y. M.; Qi, B. B.; Cui, J. G.; Gan, C. F.; Yang, C. H.; Liu, C.; Chen, S.; Shi, H. X. Chin. J. Org. Chem. 2016, 36, 1602(in Chinese).
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]
  Hao Wu , Zhen Liu , Dachang Bai . ¹H NMR Spectrum of Amide Compounds. University Chemistry, 2024, 39(3): 231-238. doi: 10.3866/PKU.DXHX202309020
4. [4]
  Chi Li , Jichao Wan , Qiyu Long , Hui Lv , Ying Xiong . N-Heterocyclic Carbene (NHC)-Catalyzed Amidation of Aldehydes with Nitroso Compounds. University Chemistry, 2024, 39(5): 388-395. doi: 10.3866/PKU.DXHX202312016
5. [5]
  Jian Li , Yu Zhang , Rongrong Yan , Kaiyuan Sun , Xiaoqing Liu , Zishang Liang , Yinan Jiao , Hui Bu , Xin Chen , Jinjin Zhao , Jianlin Shi . 高效靶向示踪钙钛矿纳米系统光电增效抗肿瘤. Acta Physico-Chimica Sinica, 2025, 41(5): 100042-. doi: 10.1016/j.actphy.2024.100042
6. [6]
  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
7. [7]
  Zhongyan Cao , Shengnan Jin , Yuxia Wang , Yiyi Chen , Xianqiang Kong , Yuanqing Xu . Advances in Highly Selective Reactions Involving Phenol Derivatives as Aryl Radical Precursors. University Chemistry, 2025, 40(4): 245-252. doi: 10.12461/PKU.DXHX202405186
8. [8]
  Hong Zheng , Xin Peng , Chunwang Yi . The Tale of Caprolactam Cyclic Oligomers: The Ever-changing Life of “Princess Cyclo”. University Chemistry, 2024, 39(9): 40-47. doi: 10.12461/PKU.DXHX202403058
9. [9]
  Yonghui ZHOU , Rujun HUANG , Dongchao YAO , Aiwei ZHANG , Yuhang SUN , Zhujun CHEN , Baisong ZHU , Youxuan ZHENG . Synthesis and photoelectric properties of fluorescence materials with electron donor-acceptor structures based on quinoxaline and pyridinopyrazine, carbazole, and diphenylamine derivatives. Chinese Journal of Inorganic Chemistry, 2024, 40(4): 701-712. doi: 10.11862/CJIC.20230373
10. [10]
  Haitang WANG , Yanni LING , Xiaqing MA , Yuxin CHEN , Rui ZHANG , Keyi WANG , Ying ZHANG , Wenmin WANG . Construction, crystal structures, and biological activities of two Ln^Ⅲ₃ complexes. Chinese Journal of Inorganic Chemistry, 2024, 40(8): 1474-1482. doi: 10.11862/CJIC.20240188
11. [11]
  Qianlang Wang , Jijun Sun , Qian Chen , Quanqin Zhao , Baojuan Xi . The Appeal of Organophosphorus Compounds: Clearing Their Name. University Chemistry, 2025, 40(4): 299-306. doi: 10.12461/PKU.DXHX202405205
12. [12]
  Ying Xiong , Guangao Yu , Lin Wu , Qingwen Liu , Houjin Li , Shuanglian Cai , Zhanxiang Liu , Xingwen Sun , Yuan Zheng , Jie Han , Xin Du , Chengshan Yuan , Qihan Zhang , Jianrong Zhang , Shuyong Zhang . Basic Operations and Specification Suggestions for Determination of Physical Constants of Organic Compounds. University Chemistry, 2025, 40(5): 106-121. doi: 10.12461/PKU.DXHX202503079
13. [13]
  Yongjian Zhang , Fangling Gao , Hong Yan , Keyin Ye . Electrochemical Transformation of Organosulfur Compounds. University Chemistry, 2025, 40(5): 311-317. doi: 10.12461/PKU.DXHX202407035
14. [14]
  Nan Xiao , Fang Sun . 二芳基硫醚化合物的构建及应用. University Chemistry, 2025, 40(6): 360-363. doi: 10.12461/PKU.DXHX202407099
15. [15]
  Xin MA , Ya SUN , Na SUN , Qian KANG , Jiajia ZHANG , Ruitao ZHU , Xiaoli GAO . A Tb₂ complex based on polydentate Schiff base: Crystal structure, fluorescence properties, and biological activity. Chinese Journal of Inorganic Chemistry, 2024, 40(7): 1347-1356. doi: 10.11862/CJIC.20230357
16. [16]
  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
17. [17]
  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
18. [18]
  Geyang Song , Dong Xue , Gang Li . Recent Advances in Transition Metal-Catalyzed Synthesis of Anilines from Aryl Halides. University Chemistry, 2024, 39(2): 321-329. doi: 10.3866/PKU.DXHX202308030
19. [19]
  Jiaming Xu , Yu Xiang , Weisheng Lin , Zhiwei Miao . Research Progress in the Synthesis of Cyclic Organic Compounds Using Bimetallic Relay Catalytic Strategies. University Chemistry, 2024, 39(3): 239-257. doi: 10.3866/PKU.DXHX202309093
20. [20]
  Aidang Lu , Yunting Liu , Yanjun Jiang . Comprehensive Organic Chemistry Experiment: Synthesis and Characterization of Triazolopyrimidine Compounds. University Chemistry, 2024, 39(8): 241-246. doi: 10.3866/PKU.DXHX202401029

Get Citation

PDF

XML

Metrics

PDF Downloads(4)
Abstract views(1045)
HTML views(114)

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