Citation: Maihesuti Liwaliding, Yu Junjie, Wang Qi, Cao Jianguo, Huang Guozheng. Synthesis and Anticancer Evaluation of Amido-Derivative of Hydnocarpin D[J]. Chinese Journal of Organic Chemistry, ;2020, 40(9): 2764-2771. doi: 10.6023/cjoc202004033 shu

Synthesis and Anticancer Evaluation of Amido-Derivative of Hydnocarpin D

a.
Key Laboratory of Plant Resources and Chemistry of Arid Zone, Xinjiang Technical Institute of Physics and Chemistry, Chinese Academy of Sciences, Urumqi 830011
b.
College of Life Sciences, Shanghai Normal University, Shanghai 201418
c.
University of Chinese Academy of Sciences, Beijing 100049

Corresponding author: Cao Jianguo, cao101@shnu.edu.cn Huang Guozheng, guozheng.huang@yahoo.com
Received Date: 21 April 2020
Revised Date: 10 June 2020
Available Online: 15 July 2020

Figures(2)

Hydnocarpins are a rare type of flavonoligan compounds occurring in nature. Because of their rarity, only a few research has been devoted on their structural modification and activity. In this work, 23-iodo hydnocarpin D was synthesized from silibinin, which is cheap and commericially available. After azidation, reduction and amidation, 15 amido-derivatives of hydnocarpin D were obtained. These compounds with regard to their anticancer activities were evaluated on three kinds of human cancer cells, and the results showed that some compounds are active on A549 with IC₅₀ values less than 10 μmol·L^-1. 23-(3, 4-Dimethoxybenzamido)hydnocarpin D (6b) and 23-(2-chloro-4-fluorobenzamido)hydnocarpin D (6f) can strongly inhibit the growth of HeLa cells. 23-(4-Fluorobenzamido)hydnocarpin D (6g) and 23-[3, 5-bis(trifluoromethyl)benzamido]-hydnocarpin D (6m) showed potent activity against MCF-7 cells. These preliminary results testified that the synthsis of amido-derivative of hydnocarpin D could be an option for the development of new anti-cancer drug candidates.
- hydnocarpin D,
- silibinin,
- structural modification,
- anticancer activity
1. [1]
  Abenavoli, L.; Capasso, R.; Milic, N.; Capasso, F. Phytother. Res. 2010, 24, 1423.
2. [2]
  Vogel, G.; Tuchweber, B.; Trost, W.; Mengs, U. Toxicol. Appl. Pharmacol. 1984, 73, 355. doi: 10.1016/0041-008X(84)90087-5
3. [3]
  Švagera, Z.; Škottová, N.; Váňa, P.; Večeřa, R.; Urbánek, K.; Belejová, M.; Kosina, P.; Šimánek, V. Phytother. Res. 2003, 17, 524. doi: 10.1002/ptr.1187
4. [4]
  Dai, J.-P.; Wu, L.-Q.; Li, R.; Zhao, X.-F.; Wan, Q.-Y.; Chen, X.-X.; Li, W.-Z.; Wang, G.-F.; Li, K.-S. Antimicrob. Agents Chemother. 2013, 57, 4433. doi: 10.1128/AAC.00759-13
5. [5]
  Agarwal, R.; Agarwal, C.; Ichikawa, H.; Singh, R. P.; Aggarwal, B. B. Anticancer Res. 2006, 26, 4457.
6. [6]
  Kim, N. C.; Graf, T. N.; Sparacino, C. M.; Wani, M. C.; Wall, M. E. Org. Biomol. Chem. 2003, 1, 1684. doi: 10.1039/b300099k
7. [7]
  Biedermann, D.; Vavříková, E.; Cvak, L.; Křen, V. Nat. Prod. Rep. 2014, 31, 1138. doi: 10.1039/C3NP70122K
8. [8]
  Guz, N. R.; Stermitz, F. R. J. Nat. Prod. 2000, 63, 1140. doi: 10.1021/np000166d
9. [9]
  Wang, J. F.; Yin, G. F.; Zhou, X. J.; Su. J.; Li, Y.; Zhong, H. M.; Duan, G.; Cheng, Y. X. J. Asian Nat. Prod. Res. 2011, 13, 80.
10. [10]
  Sharma, D.; Ranganathan, K.; Parthasarathy, M.; Bhushan, B.; Seshadri, T. R. Planta Med. 1979, 37, 79. doi: 10.1055/s-0028-1097302
11. [11]
  Parthasarathy, M. R.; Ranganathan, K. R.; Sharma, D. K. Phytochemistry 1979, 18, 506. doi: 10.1016/S0031-9422(00)81905-6
12. [12]
  Ranganathan, K. R.; Seshadri, T. R. Tetrahedron Lett. 1973, 14, 3481.
13. [13]
  Sharma, D. K.; Hall, I. H. J. Nat. Prod. 1991, 54, 1298. doi: 10.1021/np50077a010
14. [14]
  Reddy, S. V.; Tiwari, A. K.; Kumar, U. S.; Rao, R. J.; Rao, J. M. Phytother. Res. 2005, 19, 277. doi: 10.1002/ptr.1491
15. [15]
  Stermitz, F. R.; Beeson, T. D.; Mueller, P. J.; Hsiang, J. F.; Lewis, K. Biochem. Syst. Ecol. 2001, 29, 793.
16. [16]
  Stermitz, F. R.; Lorenz, P.; Tawara, J. N.; Zenewicz, L. A.; Lewis, K. Proc. Natl. Acad. Sci. U. S. A. 2000, 97, 1433. doi: 10.1073/pnas.030540597
17. [17]
  Lee, M. A.; Kim, W. K.; Park, H. J.; Kang, S. S.; Lee, S. K. Bioorg. Med. Chem. 2013, 23, 5511. doi: 10.1016/j.bmcl.2013.08.065
18. [18]
  Arya, J. S.; Joseph, M. M.; Sherin, D. R.; Nair, J. B.; Manojkumar, T. K.; Maiti, K. K. J. Med. Chem. 2019, 62, 8311. doi: 10.1021/acs.jmedchem.9b01098
19. [19]
  Huang, G.; Schramm, S.; Heilmann, J.; Biedermann, D.; Křen, V.; Decker, M. Beilstein J. Org. Chem. 2016, 12, 662. doi: 10.3762/bjoc.12.66
20. [20]
  Vimberg, V.; Kuzma, M.; Stodůlková, E.; Novák, P.; Bednárová, L.; Šulc, M.; Gažák, R. J. Nat. Prod. 2015, 78, 2095. doi: 10.1021/acs.jnatprod.5b00430
21. [21]
  Myers, A. G.; Movassaghi, M.; Zheng, B. J. Am. Chem. Soc. 1997, 119, 8572. doi: 10.1021/ja971768v
22. [22]
  Zhang, L. M.; Koreeda, M. J. Am. Chem. Soc. 2004, 126, 13190. doi: 10.1021/ja0462777
1. [1]
  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
2. [2]
  Yao HUANG , Yingshu WU , Zhichun BAO , Yue HUANG , Shangfeng TANG , Ruixue LIU , Yancheng LIU , Hong LIANG . Copper complexes of anthrahydrazone bearing pyridyl side chain: Synthesis, crystal structure, anticancer activity, and DNA binding. Chinese Journal of Inorganic Chemistry, 2025, 41(1): 213-224. doi: 10.11862/CJIC.20240359
3. [3]
  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
4. [4]
  Weina Wang , Fengyi Liu , Wenliang Wang . “Extracting Commonality, Delving into Typicals, Deriving Individuality”: Constructing a Knowledge Graph of Crystal Structures. University Chemistry, 2024, 39(3): 36-42. doi: 10.3866/PKU.DXHX202308029
5. [5]
  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
6. [6]
  Changqing MIAO , Fengjiao CHEN , Wenyu LI , Shujie WEI , Yuqing YAO , Keyi WANG , Ni WANG , Xiaoyan XIN , Ming FANG . Crystal structures, DNA action, and antibacterial activities of three tetranuclear lanthanide-based complexes. Chinese Journal of Inorganic Chemistry, 2024, 40(12): 2455-2465. doi: 10.11862/CJIC.20240192
7. [7]
  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
8. [8]
  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
9. [9]
  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
10. [10]
  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
11. [11]
  Jianjun LI , Mingjie REN , Lili ZHANG , Lingling ZENG , Huiling WANG , Xiangwu MENG . UV-assisted degradation of tetracycline hydrochloride by MnFe₂O₄@activated carbon activated persulfate. Chinese Journal of Inorganic Chemistry, 2024, 40(10): 1869-1880. doi: 10.11862/CJIC.20240187
12. [12]
  Yaping Li , Sai An , Aiqing Cao , Shilong Li , Ming Lei . The Application of Molecular Simulation Software in Structural Chemistry Education: First-Principles Calculation of NiFe Layered Double Hydroxide. University Chemistry, 2025, 40(3): 160-170. doi: 10.12461/PKU.DXHX202405185
13. [13]
  Rong Tian , Yadi Yang , Naihao Lu . Comprehensive Experimental Design of Undergraduate Students Based on Interdisciplinarity: Study on the Effect of Quercetin on Chlorination Activity of Myeloperoxidase. University Chemistry, 2024, 39(8): 247-254. doi: 10.3866/PKU.DXHX202312064
14. [14]
  Wanqun Hu , Pingping Zhu , Yuan Zheng , Wanqun Zhang , Wei Shao , Hong Wu , Qiang Zhou , Kaiping Yang , Xiang Sheng . Design and Practice of Ideological and Political Case Study in Instrumental Analysis Experiment Course: the Extraction and Structural Identification of Artemisinin. University Chemistry, 2024, 39(2): 203-207. doi: 10.3866/PKU.DXHX202310062
15. [15]
  Yuena Yang , Xufang Hu , Yushan Liu , Yaya Kuang , Jian Ling , Qiue Cao , Chuanhua Zhou . The Realm of Smart Hydrogels. University Chemistry, 2024, 39(5): 172-183. doi: 10.3866/PKU.DXHX202310125
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]
  Quanliang Chen , Zhaohui Zhou . Research on the Active Site of Nitrogenase over Fifty Years. University Chemistry, 2024, 39(7): 287-293. doi: 10.3866/PKU.DXHX202310133
18. [18]
  Wen YANG , Didi WANG , Ziyi HUANG , Yaping ZHOU , Yanyan FENG . La promoted hydrotalcite derived Ni-based catalysts: In situ preparation and CO₂ methanation performance. Chinese Journal of Inorganic Chemistry, 2024, 40(3): 561-570. doi: 10.11862/CJIC.20230276
19. [19]
  Ping Ye , Lingshuang Qin , Mengyao He , Fangfang Wu , Zengye Chen , Mingxing Liang , Libo Deng . 荷叶衍生多孔碳的零电荷电位调节实现废水中电化学捕集镉离子. Acta Physico-Chimica Sinica, 2025, 41(3): 2311032-. doi: 10.3866/PKU.WHXB202311032
20. [20]
  Yukai Jiang , Yihan Wang , Yunkai Zhang , Yunping Wei , Ying Ma , Na Du . Characterization and Phase Diagram of Surfactant Lyotropic Liquid Crystal. University Chemistry, 2024, 39(4): 114-118. doi: 10.3866/PKU.DXHX202309033

Get Citation

PDF

XML

Metrics

PDF Downloads(6)
Abstract views(905)
HTML views(108)

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