Citation: Liu Zhiping, Zhu Zhiling, Zheng Jiahua, Gan Chunfang, Huang Yanmin, Cui Jianguo. Syntheses and Antiproliferative Activities of (20R)-Pregn-5-ene-20-(2-methoxybenzoate) Compounds[J]. Chemistry, ;2019, 82(10): 899-908. shu

Syntheses and Antiproliferative Activities of (20R)-Pregn-5-ene-20-(2-methoxybenzoate) Compounds

Chemistry and Material Science, Nanning Normal University, Nanning 530001

Corresponding author: Huang Yanmin, huangyanmin828@163.com
Received Date: 3 June 2019
Accepted Date: 26 July 2019

Figures(2)

Using pregnenlone as a raw material, ten titled compounds and related intermediates were designed and synthesized by esterification on 3-hydroxyl and structural modification on 20-carbonyl. Their structures were characterized by IR, NMR and HRMS. The antiproliferative activities of these compounds were evaluated against HeLa (human cervical cancer), A549 (Human lung cancer), TPC-1(Human thyroid cancer), CNE-2 (nasopharyngeal carcinoma) and human HEK-293T (Normal kidney epithelial) by MTT method in vitro. The results showed that intermediates 2d and 3d display distinct antiproliferative activity against A549 with IC₅₀ of 7.9μmol/L and 10.3 μmol/L, which were not toxic to HEK-293T cells.
- Pregnenlone,
- Salicylic acid methyl ether,
- Synthesis,
- Antiproliferative activity
1. [1]
  G Aurilio, R Graffeo, V Bagnardi et al. Int. J. Clin. Monit. Comput., 2015, 20(1):90~94.
2. [2]
  K Fizazi, K N Chi. New Engl. J. Med., 2013, 368(2):138~148.
3. [3]
  Y Huang, Q Yao, J Cui et al. Chem. Res. Chin. Univ., 2014, 30(4):605~613.
4. [4]
  J G Cui, L Fan, L L Huang et al. Steroids, 2009, 74(1):62~72.
5. [5]
  C Gan, J Cui, S Su et al. Steroids, 2014, 87(9):99~107.
6. [6]
7. [7]
  J Cui, B Qi, C Gan et al. Marine Drugs, 2015, 13(4):2488~2504.
8. [8]
  M Hossain, D N Kirk. Steroids, 1979, 34(6):677~681.
9. [9]
  M PKatarina, A D Evgenija, S Mihaly. Steroids, 2015, 94:31~40.
10. [10]
  R C Schmeltzer, T J Anastasiou, K E Uhrich. Polym. Bull., 2003, 49(6):441~448.
11. [11]
  O Soltani, J K De Brabander. Angew. Chem., 2010, 117(11):1724~1727.
12. [12]
  Z Zhang, C Jia, Y Hu. Toxicol. Lett., 2012, 209(2):146~153.
13. [13]
14. [14]
  F K Yoshimoto, H D Arman, W P Griffith. Steroids, 2017, 128:50~57.
15. [15]
  F Weber, N P Weitkamp, K Mukherjee. Fresen Environ. Bull., 2003, 12:517~522.
16. [16]
  R Castelli, A Giacomini, M F Anselmi. J. Med. Chem., 2016, 59(10):4651~4664.
17. [17]
18. [18]
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]
  Xinting XIONG , Zhiqiang XIONG , Panlei XIAO , Xuliang NIE , Xiuying SONG , Xiuguang YI . Synthesis, crystal structures, Hirshfeld surface analysis, and antifungal activity of two complexes Na(Ⅰ)/Cd(Ⅱ) assembled by 5-bromo-2-hydroxybenzoic acid ligands. Chinese Journal of Inorganic Chemistry, 2024, 40(9): 1661-1670. doi: 10.11862/CJIC.20240145
3. [3]
  Bin SUN , Heyan JIANG . Glucose-modified bis-Schiff bases: Synthesis and bio-activities in Alzheimer′s disease therapy. Chinese Journal of Inorganic Chemistry, 2025, 41(7): 1338-1350. doi: 10.11862/CJIC.20240428
4. [4]
  Lifang HE , Wenjie TANG , Yaoze LUO , Mingsheng LIANG , Jianxin TANG , Yuxuan WU , Fuxing ZHANG , Xiaoming ZHU . Synthesis, structure, and anticancer activity of two dialkyltin complexes constructed based on 2, 2′-bipyridin-6, 6′-dicarboxylic acid. Chinese Journal of Inorganic Chemistry, 2025, 41(8): 1601-1609. doi: 10.11862/CJIC.20250012
5. [5]
  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
6. [6]
  Xinyi Zhang , Kai Ren , Yanning Liu , Zhenyi Gu , Zhixiong Huang , Shuohang Zheng , Xiaotong Wang , Jinzhi Guo , Igor V. Zatovsky , Junming Cao , Xinglong Wu . Progress on Entropy Production Engineering for Electrochemical Catalysis. Acta Physico-Chimica Sinica, 2024, 40(7): 2307057-0. doi: 10.3866/PKU.WHXB202307057
7. [7]
  Lei Feng , Ze-Min Zhu , Ying Yang , Zongbin He , Jiafeng Zou , Man-Bo Li , Yan Zhao , Zhikun Wu . Long-Pursued Structure of Au₂₃(S-Adm)₁₆ and the Unexpected Doping Effects. Acta Physico-Chimica Sinica, 2024, 40(5): 2305029-0. doi: 10.3866/PKU.WHXB202305029
8. [8]
  Chunling Qin , Shuang Chen , Hassanien Gomaa , Mohamed A. Shenashen , Sherif A. El-Safty , Qian Liu , Cuihua An , Xijun Liu , Qibo Deng , Ning Hu . Regulating HER and OER Performances of 2D Materials by the External Physical Fields. Acta Physico-Chimica Sinica, 2024, 40(9): 2307059-0. doi: 10.3866/PKU.WHXB202307059
9. [9]
  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
10. [10]
  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
11. [11]
  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
12. [12]
  Mengyang LI , Hao XU , Zhonghao NIU , Chunhua GONG , Weihui ZHONG , Jingli XIE . Highly effective catalytic synthesis of β-amino alcohols by using viologen-polyoxometalate hybrid materials. Chinese Journal of Inorganic Chemistry, 2025, 41(7): 1294-1300. doi: 10.11862/CJIC.20250080
13. [13]
  Liping GUO . Synthesis and crystal structure characterization of yttrium imido complex: The reactivity of 2-substituted-1-amino-o-carborane with yttrium dialkyl complex. Chinese Journal of Inorganic Chemistry, 2025, 41(7): 1409-1415. doi: 10.11862/CJIC.20250065
14. [14]
  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
15. [15]
  Qingying Gao , Tao Luo , Jianyuan Su , Chaofan Yu , Jiazhu Li , Bingfei Yan , Wenzuo Li , Zhen Zhang , Yi Liu . Refinement and Expansion of the Classic Cinnamic Acid Synthesis Experiment. University Chemistry, 2024, 39(5): 243-250. doi: 10.3866/PKU.DXHX202311074
16. [16]
  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
17. [17]
  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
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]
  Rui Gao , Ying Zhou , Yifan Hu , Siyuan Chen , Shouhong Xu , Qianfu Luo , Wenqing Zhang . Design, Synthesis and Performance Experiment of Novel Photoswitchable Hybrid Tetraarylethenes. University Chemistry, 2024, 39(5): 125-133. doi: 10.3866/PKU.DXHX202310050
20. [20]
  Yongqing Kuang , Jie Liu , Jianjun Feng , Wen Yang , Shuanglian Cai , Ling Shi . Experimental Design for the Two-Step Synthesis of Paracetamol from 4-Hydroxyacetophenone. University Chemistry, 2024, 39(8): 331-337. doi: 10.12461/PKU.DXHX202403012

Get Citation

PDF

XML

Metrics

PDF Downloads(0)
Abstract views(1512)
HTML views(63)

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