Citation: Yu Tingting, Li Lei, Cui Huabo, Meng Yanqiu. Syntheses and Antitumor Activities of Ursolic Acid C-3, C-28 Derivatives[J]. Chemistry, ;2017, 80(11): 1055-1060. shu

Syntheses and Antitumor Activities of Ursolic Acid C-3, C-28 Derivatives

Department of Pharmaceutical Engineering, Shenyang University of Chemical Technology, Shenyang 110142

Corresponding author: Meng Yanqiu, myq6581@163.com
Received Date: 17 April 2017
Accepted Date: 30 August 2017

Figures(1)

Eleven unreported ursolic acid derivatives were designed and synthesized by the oxidation, acylation and esterification of natural product ursolic acid, meantime their structures were characterized by MS, ¹H NMR and elemental analysis. A549 and SGC-7901 cells were used to screen the anti-tumor activity in vitro through the MTT assay. The results indicated that the inhibitory rates of the target compounds on A549 and SGC-7901 cells were significantly higher than that of ursolic acid, especially the inhibitory activities of the compounds 4b and 5a are higher than that of 5-Fu and Gefitinib, which are worthy of further research endeavours.
- Ursolic acid,
- Synthesis,
- Anti-tumor activity
1. [1]
2. [2]
  W Liu. Molecules, 2012, 17(8):9104~9115.
3. [3]
  Y R Jin, J L Jin, C H Li et al. Pharm. Biol., 2012, 50(4):523~528.
4. [4]
  S Fontanay, M Grare, J Mayer et al. J. Ethnopharmacol., 2008, 120(2):272~276.
5. [5]
  O B Kazakova, E Y Giniyatullina G V Yamansarov et al. Bioorg. Med. Chem., 2010, 20(4):4088~4090.
6. [6]
7. [7]
  R R Ortizandrade, S Garcíajiménez, P Castilloespaña et al. J. Ethnopharmacol., 2007, 109(1):48~53.
8. [8]
9. [9]
10. [10]
  M H Shyu, T C Kao, G C Yen. J. Agric. Food. Chem., 2010, 58(10):6110~6118.
11. [11]
  Y X Zhang, C Z Kong, L H Wang et al. J. Cell. Biochem., 2010, 109(4):764~773.
12. [12]
  Y Zhang, C Kong, Y Zeng et al. Mol. Carcinogen., 2010, 49(4):374~385.
13. [13]
  P O Harmand, R Duval, B Liagre et al. Int. J. Oncol., 2003, 23(1):105~112.
14. [14]
  I Bonaccorsi, F Altieri, I Sciamanna et al. Cancer Lett., 2008, 263(1):130~139.
15. [15]
  S J Tsai, M C Yin. J. Food Sci., 2008, 73(7):H174~H178.
16. [16]
  M Kanjoormana, G Kuttan. Integr. Cancer Ther., 2010, 9(2):224~235.
17. [17]
  S L Yan, C Y Huang, S T Wu et al. Toxicol. In Vitro, 2010, 24(3):842~848.
18. [18]
  H J You, C Y Choi, J Y Kim et al. Febs Lett., 2001, 509(2):156~160.
19. [19]
  Y Q Meng, D Liu, L L Cai et al. Bioorg. Med. Chem., 2009, 17(2):848~854.
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]
  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
11. [11]
  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
12. [12]
  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
13. [13]
  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
14. [14]
  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
15. [15]
  Jingjing QING , Fan HE , Zhihui LIU , Shuaipeng HOU , Ya LIU , Yifan JIANG , Mengting TAN , Lifang HE , Fuxing ZHANG , Xiaoming ZHU . Synthesis, structure, and anticancer activity of two complexes of dimethylglyoxime organotin. Chinese Journal of Inorganic Chemistry, 2024, 40(7): 1301-1308. doi: 10.11862/CJIC.20240003
16. [16]
  Hong RAO , Yang HU , Yicong MA , Chunxin LÜ , Wei ZHONG , Lihua DU . Synthesis and in vitro anticancer activity of phenanthroline-functionalized nitrogen heterocyclic carbene homo- and heterobimetallic silver/gold complexes. Chinese Journal of Inorganic Chemistry, 2024, 40(12): 2429-2437. doi: 10.11862/CJIC.20240275
17. [17]
  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
18. [18]
  Minna Ma , Yujin Ouyang , Yuan Wu , Mingwei Yuan , Lijuan Yang . Green Synthesis of Medical Chemiluminescence Reagents by Photocatalytic Oxidation. University Chemistry, 2024, 39(5): 134-143. doi: 10.3866/PKU.DXHX202310093
19. [19]
  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
20. [20]
  Wenjun Zheng . Application in Inorganic Synthesis of Ionic Liquids. University Chemistry, 2024, 39(8): 163-168. doi: 10.3866/PKU.DXHX202401020

Get Citation

PDF

XML

Metrics

PDF Downloads(8)
Abstract views(1173)
HTML views(208)

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