Citation: Shang Fanfan, Jin Lan, Zhang Haibin, Piao Lianxun, Quan Zheshan. Synthesis and Anti-toxoplasma Activity in Vitro of Chrysin Derivatives[J]. Chinese Journal of Organic Chemistry, ;2019, 39(9): 2574-2580. doi: 10.6023/cjoc201901016 shu

Synthesis and Anti-toxoplasma Activity in Vitro of Chrysin Derivatives

College of Pharmacy, Yanbian University, Yanji 133002

Corresponding author: Piao Lianxun, lxpiao@ybu.edu.cn Quan Zheshan, zsquan@ybu.edu.cn
Received Date: 11 January 2019
Revised Date: 28 February 2019
Available Online: 21 September 2019
Fund Project: the National Natural Science Foundation of China 21662036the National Natural Science Foundation of China 81660344Project supported by the National Natural Science Foundation of China (Nos. 21662036, 81660344)

Figures(2)

In this paper, 18 novel chrysin derivatives were designed and synthesized. All target compounds were tested for anti-Toxoplasma activity by methyl thiazolyl tetrazolium (MTT) colorimetric method. The chemical structures were characterized by ¹H NMR, ¹³C NMR and HRMS spectra. The selectivity index of 5-hydroxy-7-methoxy-4-oxo-N, 2-diphenyl-4H-chro-mene-8-sulfonamide (D2) was 1.76, indicating that the anti-toxoplasma activity of compound D2 was significantly higher than that of the lead compound chrysin and the positive control drug sulfadiazine.
- chrysin derivatives,
- synthesis,
- toxoplasma activity,
- in vitro,
- selectivity index
1. [1]
  Rostami, A.; Riahi, S. M.; Fakhri, Y.; Saber, V; Hanifehpour, H; Valizadeh, S; Gholizadeh, M; Pouya, R. H.; Gamble, H. R. Vet. Parasitol. 2017, 244, 12. doi: 10.1016/j.vetpar.2017.07.013
2. [2]
  Cheng, W.; Wang, C.; Xu, T.; Liu, F.; Pappoe, F.; Luo, Q. L.; Xu, Y. H.; Lu, F. L.; Shen, J. L Vet.Parasitol. 2017, 10, 580.
3. [3]
  Flegr, J.; Prandota, J.; Soviková, M; Israili, Z. H. Plosone 2014, 9, e90203. doi: 10.1371/journal.pone.0090203
4. [4]
  Hill, D. E.; Dubey, J. P. Microbiol. Spectr. 2016, 4, 1.
5. [5]
  Mui, E. J.; Jacobus, D.; Milhous, W. K.; Schiehser, G.; Hsu, H.; Roberts, C. W.; Kirisits, M. J.; McLeod, R. Antimicrob. Agents Chemother. 2005, 49, 3463. doi: 10.1128/AAC.49.8.3463-3467.2005
6. [6]
  Derouin, F.; Jacqz-Aigrain, E.; Thulliez, P.; Couvreur, J.; Leport, C. Parasitol. Today 2002, 16, 254.
7. [7]
  Sak, K. Asian Pac. J. Cancer Prev. 2014, 15, 8007. doi: 10.7314/APJCP.2014.15.19.8007
8. [8]
  Feng, X.; Qin, H.; Shi, Q.; Zhang, Y.; Zhou, F. F.; Wu, H. C.; Ding, S.; Niu, Z. Y.; Lu, Y.; Shen, P. P. Biochem. Pharmacol. 2014, 89, 503. doi: 10.1016/j.bcp.2014.03.016
9. [9]
  Chan, E. C. H.; Patchareewan, P.; Owen, L.; Cardiovasc, W. J. Pharmacol. 2000, 35, 326.
10. [10]
  Lee, J. H.; Kim, Y. S.; Lee, C. K.; Lee, H. K.; Han, S.; Saengyak Hakhoechi, S. Chem. Chemother. 1999, 30, 34.
11. [11]
  Shin, J. S.; Kim, K. S.; Kim, M. B.; Jeong, J. H.; Kim, B. K. Bioorg. Med. Chem. Lett. 1999, 9, 869. doi: 10.1016/S0960-894X(99)00092-X
12. [12]
  Zanoli, P.; Avallone, R.; Baraldi, M. Fitoterapia 2000, 71, 117. doi: 10.1016/S0367-326X(00)00186-6
13. [13]
  Adeyemi, O. S.; Sugi, T.; Han, Y. M.; Kato, K. Parasitol. Res. 2018, 117, 355. doi: 10.1007/s00436-017-5698-1
14. [14]
  Chio, L. C.; Bolyard, L. A.; Nasr, M. Antimicrob. Agents Chemother. 1996, 40, 727. doi: 10.1128/AAC.40.3.727
15. [15]
  Yeo, S. J.; Jin, C. M.; Kim, S. Y.; Park, H. Korean J. Parasitol. 2016, 54, 155. doi: 10.3347/kjp.2016.54.2.155
16. [16]
  Lu, K, ; Chu, J.; Wang, H. M.; Fu, X. l; Quan, D. W.; Ding, H. X.; Yao, Q. W.; Yu, P. Tetrahedron Lett. 2013, 54, 6345. doi: 10.1016/j.tetlet.2013.09.051
17. [17]
  Li, Y. Q.; Zhao, W. J.; Song, Q. L.; Zhang, X. F.; Li, Z. CN 103214444, 2015.
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]
  Zhongyan Cao , Shengnan Jin , Yuxia Wang , Yiyi Chen , Xianqiang Kong , Yuanqing Xu . Advances in Highly Selective Reactions Involving Phenol Derivatives as Aryl Radical Precursors. University Chemistry, 2025, 40(4): 245-252. doi: 10.12461/PKU.DXHX202405186
5. [5]
  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
6. [6]
  Shihui Shi , Haoyu Li , Shaojie Han , Yifan Yao , Siqi Liu . Regioselectively Synthesis of Halogenated Arenes via Self-Assembly and Synergistic Catalysis Strategy. University Chemistry, 2024, 39(5): 336-344. doi: 10.3866/PKU.DXHX202312002
7. [7]
  Xilin Zhao , Xingyu Tu , Zongxuan Li , Rui Dong , Bo Jiang , Zhiwei Miao . Research Progress in Enantioselective Synthesis of Axial Chiral Compounds. University Chemistry, 2024, 39(11): 158-173. doi: 10.12461/PKU.DXHX202403106
8. [8]
  Junjie Zhang , Yue Wang , Qiuhan Wu , Ruquan Shen , Han Liu , Xinhua Duan . Preparation and Selective Separation of Lightweight Magnetic Molecularly Imprinted Polymers for Trace Tetracycline Detection in Milk. University Chemistry, 2024, 39(5): 251-257. doi: 10.3866/PKU.DXHX202311084
9. [9]
  Yinuo Wang , Siran Wang , Yilong Zhao , Dazhen Xu . Selective Synthesis of Diarylmethyl Anilines and Triarylmethanes via Multicomponent Reactions: Introduce a Comprehensive Experiment of Organic Chemistry. University Chemistry, 2024, 39(8): 324-330. doi: 10.3866/PKU.DXHX202401063
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]
  Yunhao Zhang , Yinuo Wang , Siran Wang , Dazhen Xu . Progress in Selective Construction of Functional Aromatics from Nitrogenous Cycloalkanes. University Chemistry, 2024, 39(11): 136-145. doi: 10.3866/PKU.DXHX202401083
12. [12]
  Peiran ZHAO , Yuqian LIU , Cheng HE , Chunying DUAN . A functionalized Eu³⁺ metal-organic framework for selective fluorescent detection of pyrene. Chinese Journal of Inorganic Chemistry, 2024, 40(4): 713-724. doi: 10.11862/CJIC.20230355
13. [13]
  Jiakun BAI , Ting XU , Lu ZHANG , Jiang PENG , Yuqiang LI , Junhui JIA . A red-emitting fluorescent probe with a large Stokes shift for selective detection of hypochlorous acid. Chinese Journal of Inorganic Chemistry, 2024, 40(6): 1095-1104. doi: 10.11862/CJIC.20240002
14. [14]
  .
  CCS Chemistry | 超分子活化底物为自由基促进高效选择性光催化氧化
  . CCS Chemistry, 2025, 7(10.31635/ccschem.025.202405229): -.
15. [15]
  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
16. [16]
  Jun LUO , Baoshu LIU , Yunchang ZHANG , Bingkai WANG , Beibei GUO , Lan SHE , Tianheng CHEN . Europium(Ⅲ) metal-organic framework as a fluorescent probe for selectively and sensitively sensing Pb²⁺ in aqueous solution. Chinese Journal of Inorganic Chemistry, 2024, 40(12): 2438-2444. doi: 10.11862/CJIC.20240240
17. [17]
  Jie ZHAO , Sen LIU , Qikang YIN , Xiaoqing LU , Zhaojie WANG . Theoretical calculation of selective adsorption and separation of CO₂ by alkali metal modified naphthalene/naphthalenediyne. Chinese Journal of Inorganic Chemistry, 2024, 40(3): 515-522. doi: 10.11862/CJIC.20230385
18. [18]
  Peng YUE , Liyao SHI , Jinglei CUI , Huirong ZHANG , Yanxia GUO . Effects of Ce and Mn promoters on the selective oxidation of ammonia over V₂O₅/TiO₂ catalyst. Chinese Journal of Inorganic Chemistry, 2025, 41(2): 293-307. doi: 10.11862/CJIC.20240210
19. [19]
  Baitong Wei , Jinxin Guo , Xigong Liu , Rongxiu Zhu , Lei Liu . Theoretical Study on the Structure, Stability of Hydrocarbon Free Radicals and Selectivity of Alkane Chlorination Reaction. University Chemistry, 2025, 40(3): 402-407. doi: 10.12461/PKU.DXHX202406003
20. [20]
  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

Get Citation

PDF

XML

Metrics

PDF Downloads(5)
Abstract views(1126)
HTML views(135)

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