Citation: Lin Yuping, Hu Chunyan, Zheng Xi, Wang Xiuli, Wan Chunping, Mao Zewei. Synthesis and Anti-tumor Activities of Novel 4'-(N-Substitued-1-piperazinyl) chalcone Derivatives[J]. Chinese Journal of Organic Chemistry, ;2017, 37(1): 237-241. doi: 10.6023/cjoc201605021 shu

Synthesis and Anti-tumor Activities of Novel 4'-(N-Substitued-1-piperazinyl) chalcone Derivatives

Lin Yuping ^a ,
Hu Chunyan ^a ,
Zheng Xi ^b ,
Wang Xiuli ^a ,
Wan Chunping ^b ,
Mao Zewei ^a,*,,

a.
School of Traditional Chinese Medicine, Yunnan University of Traditional Chinese Medicine, Kunming 650500
b.
Central Laboratory, The No. 1 Affiliated Hospital of Yunnan University of Traditional Chinese Medicine, Kunming 650021

Corresponding author: Mao Zewei, ydmason@163.com
Received Date: 12 May 2016
Revised Date: 20 June 2016

Fund Project: the National Natural Science Foundation of China 81460624the Foundation of Yunnan Province Department of Education 2014Z119

Figures(2)

With the aim of developing new potent anticancer agents, a series of novel 4'-(N-substitued-1-piperazinyl) chalcone derivatives 3a~3j have been designed and synthesized based on the structure of the chalcone by molecular hybridization.The structures were characterized by ¹H NMR, ¹³C NMR and HRMS.These derivatives were evaluated for their in vitro anti-tumor activity against a panel of human tumor cell lines (Hela, A549 and SGC7901) by the thiazolyl blue tetrazolium bromide (MTT) assay.The result indicated that compounds 3f, 3i and 3j were found to be the potent compounds against human tumor cell lines, which are to be lead compounds for further structural modifications and activity research.
- chalcone,
- piperazine,
- synthesis,
- anti-tumor activity
1. [1]
  Ayabe, S.; Furuya, T. Tetrahedron Lett. 1981, 22, 2097. doi: 10.1016/S0040-4039(01)93286-1
2. [2]
  Kim, N. Y.; Pae, H. O.; Oh, G. S.; Kang, T. H.; Kim, Y. C.; Rhew, H. Y.; Chung, H. T. Pharmacol. Toxicol. 2001, 88, 261. doi: 10.1034/j.1600-0773.2001.d01-114.x
3. [3]
  Jayasinghe, L.; Balasooriya, B. A. I. S.; Padmini, W. C.; Hara, N.; Fujimoto, Y. Phytochemistry 2004, 65, 1287. doi: 10.1016/j.phytochem.2004.03.033
4. [4]
  Kim, K. N.; Ko, Y. J.; Kang, M. C.; Yang, H. M.; Roh, S. W.; Oda, T.; Jeon, Y. J.; Jung, W. K.; Heo, S. J.; Yoon, W. J.; Kim, D. Food Chem. Toxicol. 2013, 53, 371. doi: 10.1016/j.fct.2012.12.021
5. [5]
  Franco, C.; Rossella, F.; Adriana, B.; Paola, C.; Daniela, O. S.; Francesca, R.; Matilde, Y.; Francesco, O.; Stefano. A. J. Med. Chem. 2009, 52, 2818. doi: 10.1021/jm801590u
6. [6]
  Shen, Y. N.; Lin, L.; Qiu, H. Y.; Zou, W. Y.; Qian, Y.; Zhu, H. L. RSC Adv. 2015, 5, 23767. doi: 10.1039/C4RA12108B
7. [7]
  Sashidhara, K. V.; Kumar, M.; Modukuri, R. K.; Sonkar, R.; Bhatia, G.; Khanna, A. K.; Rai, S.; Shukla, R. Bioorg. Med. Chem. Lett. 2011, 21, 4480. doi: 10.1016/j.bmcl.2011.06.002
8. [8]
  Mishra, N.; Arora, P.; Kumar, B.; Mishra, L. C.; Bhattacharya, A.; Awasthi, S. K.; Bhasin, V. K. Eur. J. Med. Chem. 2008, 43, 1530. doi: 10.1016/j.ejmech.2007.09.014
9. [9]
  Fang, X. W.; Zhou, L. Z.; Cheng, Z.; Yang, M. P.; Yang, B. Q. Chin. J. Org. Chem. 2013, 33, 523(in Chinese). doi: 10.6023/cjoc201211041
10. [10]
  Dai, H.; Miao, W. K.; Liu, J. B.; Wu, S. S.; Qin, X.; Fang, J. X. Chin. J. Org. Chem. 2012, 32, 1690(in Chinese). doi: 10.6023/cjoc1202211
11. [11]
  Vergelli, C.; Ciciani, G.; Cilibrizzi, A.; Crocetti, L.; Mannelli, L. D.; Ghelardini, C.; Guerrini, G.; Iacovone, A.; Giovannoni, M. P. Bioorg. Med. Chem. 2015, 23, 6237. doi: 10.1016/j.bmc.2015.08.043
12. [12]
  Safrygin, A. V.; Irgashev, R. A.; Barabanov, M. A.; Sosnovskikh, V. Y. Tetrahedron 2016, 72, 227. doi: 10.1016/j.tet.2015.11.037
13. [13]
  Biswas, N. N.; Kutty, S. K.; Iskander, G. M.; Mielczarek, M.; Bhadbhade, M. M.; Gardner, C. R.; Black, D. S.; Kumar, N. Tetrahedron 2016, 72, 539. doi: 10.1016/j.tet.2015.12.018
14. [14]
  Edlund, C.; Oh, H.; Nord, C. E. Clin. Microbiol. Infect. 1999, 1, 51. doi: 10.1016/S1286-4579(99)80014-8
15. [15]
  Fasciolo, G.; Nicolini, A.; Vacca, N.; Viglierchio, P. Curr. Ther. Res. 1994, 3, 251.
16. [16]
  Mao, Z. W.; Zheng, X.; Qi, Y.; Zhang, M. D.; Huang, Y.; Wan, C. P.; Rao, G. X. RSC Adv. 2016, 6, 7723. doi: 10.1039/C5RA20197G
17. [17]
  Watson, A. J.; Fairbanks, A. J. Eur. J. Org. Chem. 2013, 30, 6784.
18. [18]
  Kantam, M. L.; Yadav, J.; Laha, S.; Sreedhar, B.; Jha, S. Adv. Synth. Catal. 2007, 349, 1938. doi: 10.1002/(ISSN)1615-4169
19. [19]
  Ajay, A.; Singh, V.; Singh, S.; Pandey, S.; Gunjan, S.; Dubey, D.; Sinha, S. K.; Singh, B. N.; Chaturvedi, V.; Tripathi, R.; Ramchandran, R.; Tripathi, R. P. Bioorg. Med. Chem. 2010, 23, 8289.
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]
  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
4. [4]
  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
5. [5]
  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
6. [6]
  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
7. [7]
  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
8. [8]
  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
9. [9]
  Yurong Tang , Yunren Shi , Yi Xu , Bo Qin , Yanqin Xu , Yunfei Cai . Innovative Experiment and Course Transformation Practice of Visible-Light-Mediated Photocatalytic Synthesis of Isoquinolinone. University Chemistry, 2024, 39(5): 296-306. doi: 10.3866/PKU.DXHX202311087
10. [10]
  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
11. [11]
  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
12. [12]
  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
13. [13]
  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
14. [14]
  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
15. [15]
  Wenjun Zheng . Application in Inorganic Synthesis of Ionic Liquids. University Chemistry, 2024, 39(8): 163-168. doi: 10.3866/PKU.DXHX202401020
16. [16]
  Hongyan Chen , Yajun Hou , Shui Hu , Zhuoxun Wei , Fang Zhu , Chengyong Su . Construction of Synthetic Chemistry Experiment of the Chemistry “101 Plan”. University Chemistry, 2024, 39(10): 58-63. doi: 10.12461/PKU.DXHX202409109
17. [17]
  Huijuan Liao , Yulin Xiao , Dong Xue , Mingyu Yang , Jianyang Dong . Synthesis of 1-Benzyl Isoquinoline via the Minisci Reaction. University Chemistry, 2025, 40(7): 294-299. doi: 10.12461/PKU.DXHX202409092
18. [18]
  Cunming Yu , Dongliang Tian , Jing Chen , Qinglin Yang , Kesong Liu , Lei Jiang . Chemistry “101 Program” Synthetic Chemistry Experiment Course Construction: Synthesis and Properties of Bioinspired Superhydrophobic Functional Materials. University Chemistry, 2024, 39(10): 101-106. doi: 10.12461/PKU.DXHX202408008
19. [19]
  Jiaojiao Yu , Bo Sun , Na Li , Cong Wen , Wei Li . Improvement of Classical Organic Experiment Based on the “Reverse-Step Optimization Method”: Taking Synthesis of Ethyl Acetate as an Example. University Chemistry, 2025, 40(3): 333-341. doi: 10.12461/PKU.DXHX202405177
20. [20]
  Yuan Zheng , Quan Lan , Zhenggen Zha , Lingling Li , Jun Jiang , Pingping Zhu . Teaching Reform of Organic Synthesis Experiments by Introducing Reverse Thinking and Design Concepts: Taking the Synthesis of Cinnamic Acid Based on Retrosynthetic Analysis as an Example. University Chemistry, 2024, 39(6): 207-213. doi: 10.3866/PKU.DXHX202310065

Get Citation

PDF

XML

Metrics

PDF Downloads(3)
Abstract views(942)
HTML views(125)

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