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

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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]
  Huilin ZHENG , Tao WANG , Ruilin GAO , Mengke ZHOU , Xinyue LI , Hui WANG , Xiaoxia GU . Antitumor and antibacterial activities of transition metal complexes incorporating pyridyl salicylaldehyde Schiff base. Chinese Journal of Inorganic Chemistry, 2026, 42(5): 897-905. doi: 10.11862/CJIC.20250358
3. [3]
  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
4. [4]
  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
5. [5]
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6. [6]
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7. [7]
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8. [8]
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9. [9]
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10. [10]
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11. [11]
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12. [12]
  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
13. [13]
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14. [14]
  Sihan Wang , Chenxi Yu , Shuzhang Ran , Jiawei Chen , Shoutong Rao , Xinyi Liang , Ruiqi Dong , Guixiang Zeng , Guoqiang Wang , Jing Ma . 铁配合物合成与性质探究的数智化改进——大学化学实验中“磺基水杨酸合铁配合物的组成与稳定常数的测定”的创新设计. University Chemistry, 2026, 41(5): 36-49. doi: 10.12461/PKU.DXHX202511137
15. [15]
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16. [16]
  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
17. [17]
  Jingxuan Zhang , Weihao Jiang , Siyuan Zhang , Hongye Tian , Ziye Huang , Lin Huang , Qikun Wu , Jing Yang , Yibin Jiang , Cheng Wang . Automation and AI-Assisted Investigation of the Chemical Reactivity of Sulfosalicylic Acid. University Chemistry, 2026, 41(1): 332-345. doi: 10.12461/PKU.DXHX202505108
18. [18]
  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
19. [19]
  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
20. [20]
  Lifang HE , Yaoze LUO , Qiying SHI , Jianxin TANG , Fuxing ZHANG , Xiaoming ZHU . Synthesis, structure, and properties of hydrated tricyclohexyltin theophylline-7-acetic acid complex. Chinese Journal of Inorganic Chemistry, 2026, 42(3): 632-640. doi: 10.11862/CJIC.20250244

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