Citation: Liu Ming, Liu Yang, Liu Ailin, Zhang Dongkai, Chen Minggui, Wu Changchun, Hua Xuewen, Zhou Sha, Li Zhengming. Synthesis and Bioactivities of Novel Coumarin Derivatives Containing Sulfinic Esters or Sulfinamide Moiety[J]. Chinese Journal of Organic Chemistry, ;2016, 36(7): 1653-1661. doi: 10.6023/cjoc201601011 shu

Synthesis and Bioactivities of Novel Coumarin Derivatives Containing Sulfinic Esters or Sulfinamide Moiety

Liu Ming ^a ,
Liu Yang ^a ,
Liu Ailin ^b ,
Zhang Dongkai ^a ,
Chen Minggui ^a ,
Wu Changchun ^a ,
Hua Xuewen ^a ,
Zhou Sha ^a ,
Li Zhengming ^a,*,,

a.
State Key Laboratory of Elemento-organic Chemistry, Collaborative Innovation Center of Chemical Science and Engineering (Tianjin), Institute of Elemento-organic Chemistry, Nankai University, Tianjin 300071
b.
Institute of Materia Medica, Chinese Academy of Medical Science and Peking Union Medical College, Beijing 100050

Corresponding author: Li Zhengming, nkzml@vip.163.com
Received Date: 11 January 2016
Revised Date: 22 February 2016

Fund Project: the “111” Project of Ministry of Education of China No. B06005

Figures(2)

A series of novel coumarin derivatives containing sulfinic esters or sulfonamide were designed and synthesized. Their structures were characterized by ¹H NMR, ¹³C NMR and elemental analysis. The preliminary bioassays indicated that several target compounds exhibited good in vitro antitumor activities on A549 (up to 67.82%), Bel7402 (up to 58.47%) and HCT-8 (up to 74.80%) at 5.0 mg/L and moderate antifungal activities on Physalospora piricola (up to 82.0 %) at 50 mg/L. The structure-activity relationship of these target compounds was discussed accordingly.
- coumarin,
- sulfinic esters,
- sulfinamide,
- anticancer activity,
- antifungal activity
1. [1]
  Liu, M.; Liu, Y.; Hua, X.; Wu, C.; Zhou, S.; Wang, B.; Li, Z. Chin. J. Chem. 2015, 33, 1353.
2. [2]
3. [3]
  Xu, Y.-M.; Liu, M. X.; Grunow, N.; Wijeratne, E. M. K.; Paine-Murrieta, G.; Felder, S.; Kris, R. M.; Gunatilaka, A. A. L. J. Med. Chem. 2015, 58, 6984.
4. [4]
  Ma, Q.; Liu, Y.; Zhang, P.; Li, Y.; Xiong, L.; Wang, Q. J. Agric. Food Chem. 2014, 62, 6072.
5. [5]
  Han, Y.; Ding, Y.; Xie, D.; Hu, D.; Li, P.; Li, X.; Xue, W.; Jin, L.; Song, B. Eur. J. Med. Chem. 2015, 92, 732.
6. [6]
7. [7]
8. [8]
  Liu, M.-M.; Chen, X.-Y.; Huang, Y.-Q.; Feng, P.; Guo, Y.-L.; Yang, G.; Chen, Y. J. Med. Chem. 2014, 57, 9343.
9. [9]
  Thakur, A.; Singla, R.; Jaitak, V. Eur. J. Med. Chem. 2015, 101, 476.
10. [10]
  Nasr, T.; Bondock, S.; Youns, M. Eur. J. Med. Chem. 2014, 76, 539.
11. [11]
  Städler, E.; Buser, H.-R. Experientia 1984, 40, 1157.
12. [12]
  Wang, C.-M.; Guan, W.; Fang, S.; Chen, H.; Li, Y.-Q.; Cai, C.; Fan, Y.-J.; Shi, Z.-Q. J. Asian Nat. Prod. Res. 2010, 12, 672.
13. [13]
  Kwon, Y.-S.; Kobayashi, A.; Kajiyama, S.-I.; Kawazu, K.; Kanzaki, H.; Kim, C.-M. Phytochemistry 1997, 44, 887.
14. [14]
  Venugopala, K. N.; Rashmi, V.; Odhav, B. BioMed Res. Int. 2013, 2013, 963248.
15. [15]
  Kenchappa, R.; Bodke, Y.; Peethambar, S. K.; Telkar, S.; Bhovi, V. Med. Chem. Res. 2013, 22, 4787.
16. [16]
  Singh, S.; Gupta, S.; Singh, B.; Sharma, S. K.; Gupta, V. K.; Sharma, G. L. J. Proteome Res. 2012, 11, 3259.
17. [17]
18. [18]
  Guan, A.; Liu, C.; Yang, X.; Dekeyser, M. Chem. Rev. 2014, 114, 7079.
19. [19]
  Wei, J.; Sun, Z. Org. Lett. 2015, 17, 5396.
20. [20]
21. [21]
22. [22]
  Lee, J.; Gupta, S.; Huang, J.-S.; Jayathilaka, L. P.; Lee, B.-S. Anal. Biochem. 2013, 436, 187.
23. [23]
  Wang, J.; Cao, Y.; Wang, C.; Sun, B. J. Sci. Food Agric. 2011, 91, 1766.
24. [24]
  Kumar, J. A.; Saidachary, G.; Mallesham, G.; Sridhar, B.; Jain, N.; Kalivendi, S. V.; Rao, V. J.; Raju, B. C. Eur. J. Med. Chem. 2013, 65, 389.
25. [25]
  Peng, S.; Wang, L.; Huang, J.; Sun, S.; Guo, H.; Wang, J. Adv. Synth. Catal. 2013, 355, 2550.
26. [26]
  Siddiqui, N.; Ahsan, W. Eur. J. Med. Chem. 2010, 45, 1536.
27. [27]
28. [28]
1. [1]
  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
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]
  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
4. [4]
  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
5. [5]
  Chi Li , Jichao Wan , Qiyu Long , Hui Lv , Ying Xiong . N-Heterocyclic Carbene (NHC)-Catalyzed Amidation of Aldehydes with Nitroso Compounds. University Chemistry, 2024, 39(5): 388-395. doi: 10.3866/PKU.DXHX202312016
6. [6]
  Jia JI , Zhaoyang GUO , Wenni LEI , Jiawei ZHENG , Haorong QIN , Jiahong YAN , Yinling HOU , Xiaoyan XIN , Wenmin WANG . Two dinuclear Gd(Ⅲ)-based complexes constructed by a multidentate diacylhydrazone ligand: Crystal structure, magnetocaloric effect, and biological activity. Chinese Journal of Inorganic Chemistry, 2025, 41(4): 761-772. doi: 10.11862/CJIC.20240344
7. [7]
  Benhua Wang , Chaoyi Yao , Yiming Li , Qing Liu , Minhuan Lan , Guipeng Yu , Yiming Luo , Xiangzhi Song . 一种基于香豆素氟离子荧光探针的合成、表征及性能测试——“科研反哺教学”在有机化学综合实验教学中的探索与实践. University Chemistry, 2025, 40(6): 201-209. doi: 10.12461/PKU.DXHX202408070
8. [8]
  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
9. [9]
  Yuena Yu , Fang Fang . Microwave-Assisted Synthesis of Safinamide Methanesulfonate. University Chemistry, 2024, 39(11): 210-216. doi: 10.3866/PKU.DXHX202401076
10. [10]
  Caixia Lin , Ting Liu , Zhaojiang Shi , Hong Yan , Keyin Ye , Yaofeng Yuan . Innovative Experiment of Electrochemical Dearomative Spirocyclization of N-Acyl Sulfonamides. University Chemistry, 2025, 40(4): 359-366. doi: 10.12461/PKU.DXHX202406107
11. [11]
  Yufan Pan , Xue Ding , Jiayu Lin , Haiting Wu , Hairong Huang , Cuixue Chen , Meiling Ye . Oil Cosmetics, Charming Chemistry: A Gradient Science Popularization Scheme for Cream Cosmetic Preparation. University Chemistry, 2025, 40(4): 382-389. doi: 10.12461/PKU.DXHX202406078
12. [12]
  Xinhao Yan , Guoliang Hu , Ruixi Chen , Hongyu Liu , Qizhi Yao , Jiao Li , Lingling Li . Polyethylene Glycol-Ammonium Sulfate-Nitroso R Salt System for the Separation of Cobalt (II). University Chemistry, 2024, 39(6): 287-294. doi: 10.3866/PKU.DXHX202310073
13. [13]
  Bing LIU , Huang ZHANG , Hongliang HAN , Changwen HU , Yinglei ZHANG . Visible light degradation of methylene blue from water by triangle Au@TiO₂ mesoporous catalyst. Chinese Journal of Inorganic Chemistry, 2024, 40(5): 941-952. doi: 10.11862/CJIC.20230398
14. [14]
  Lijuan Wang , Yuping Ning , Jian Li , Sha Luo , Xiongfei Luo , Ruiwen Wang . Enhancing the Advanced Nature of Natural Product Chemistry Laboratory Courses with New Research Findings: A Case Study of the Application of Berberine Hydrochloride in Photodynamic Antimicrobial Films. University Chemistry, 2024, 39(11): 241-250. doi: 10.12461/PKU.DXHX202403017
15. [15]
  Junli Liu . Practice and Exploration of Research-Oriented Classroom Teaching in the Integration of Science and Education: a Case Study on the Synthesis of Sub-Nanometer Metal Oxide Materials and Their Application in Battery Energy Storage. University Chemistry, 2024, 39(10): 249-254. doi: 10.12461/PKU.DXHX202404023
16. [16]
  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
17. [17]
  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
18. [18]
  Aiai WANG , Lu ZHAO , Yunfeng BAI , Feng FENG . Research progress of bimetallic organic framework in tumor diagnosis and treatment. Chinese Journal of Inorganic Chemistry, 2024, 40(10): 1825-1839. doi: 10.11862/CJIC.20240225
19. [19]
  Tingting XU , Wenjing ZHANG , Yongbo SONG . Research advances of atomic precision coinage metal nanoclusters in tumor therapy. Chinese Journal of Inorganic Chemistry, 2024, 40(12): 2275-2285. doi: 10.11862/CJIC.20240229
20. [20]
  Jiahui CHEN , Tingting ZHENG , Xiuyun ZHANG , Wei LÜ . Research progress of near-infrared absorption inorganic nanomaterials in photothermal and photodynamic therapy of tumors. Chinese Journal of Inorganic Chemistry, 2024, 40(12): 2396-2414. doi: 10.11862/CJIC.20240106

Get Citation

PDF

XML

Metrics

PDF Downloads(0)
Abstract views(2060)
HTML views(219)

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