Citation: Gao Sufan, Zhang Yanchun, Li Jiaming, Zhang Bin, Yang Yu, Hu Mengqi. Synthesis and Biological Evaluation of Novel Phenylpropenoyl-amino Acid Derivatives[J]. Chinese Journal of Organic Chemistry, ;2019, 39(7): 1953-1961. doi: 10.6023/cjoc201812037 shu

Synthesis and Biological Evaluation of Novel Phenylpropenoyl-amino Acid Derivatives

Gao Sufan ^a,b ,
Zhang Yanchun ^a,b ,
Li Jiaming ^a,b,, ,
Zhang Bin ^a,b ,
Yang Yu ^a,b ,
Hu Mengqi ^a,b

a.
College of Pharmacy, Anhui University of Chinese Medicine, Hefei 230012
b.
Deparment of Medicinal Chemistry, Anhui Academy of Chinese Medicine, Hefei 230012

Corresponding author: Li Jiaming, lijiaming2004@sina.com
Received Date: 19 December 2018
Revised Date: 2 February 2019
Available Online: 2 July 2019
Fund Project: Project supported by the National Science and Technology Major Project in 12th Five-Year (No. 2012ZX09401-006)the National Science and Technology Major Project in 12th Five-Year 2012ZX09401-006

Figures(4)

Based on the listed drug rebamipide, a series of novel compounds of phenylpropenoyl-amino acid structures were designed and synthesized according to the pharmacophore-combination strategy. The structures of the target compounds were confirmed by NMR and MS. The inhibitory activities against IL-6 and TNF-α had been investigated. The results demonstrated that all compounds exhibited moderate IL-6 and TNF-α inhibitory activities. In particular, the activities of four compounds were significantly improved than that of rebamipide.
- IL-6,
- TNF-α,
- phenylpropenoyl-amino acid,
- synthesis
1. [1]
  Balkwill F. Nat. Rev. Cancer. 1992, 4(2), 121.
2. [2]
  Hotamisligil, G. S.; Arner, P.; Caro, J. F. J. Clin. Invest. 1995, 95(5), 2409. doi: 10.1172/JCI117936
3. [3]
  Rus H. G.; Niculescu, F.; Vlaicu, R. Atherosclerosis 1991, 89(2~3), 247.
4. [4]
  Guirado, A.; López Sánchez, J. I.; Ruiz-Alcaraz, A. J. Eur. J. Med. Chem. 2012, 54(50), 87.
5. [5]
  Hauwermeiren, F. V.; Vandenbroucke, R. E.; Libert, C. Cytokine Growth Factor. Rev. 2011, 22(5), 311.
6. [6]
  Gómez-Reino, J. J.; Carmona, L.; Valverde, V. R. Arthritis Rheum-US 2003, 48(8), 2122. doi: 10.1002/art.11137
7. [7]
  Wei, T.; Lu, Y.; Zhang, Y. Science 2011, 332(6028), 478. doi: 10.1126/science.1199214
8. [8]
  Koike, T.; Harigai, M.; Inokuma, S. Ann. Rheum. Dis. 2011, 70(12), 2148. doi: 10.1136/ard.2011.151092
9. [9]
  Desai, S. B.; Furst, D. E. Best Pract. Res., Clin. Rheumatol. 2006, 20(4), 757. doi: 10.1016/j.berh.2006.06.002
10. [10]
  Bandgarab, B. P.; Korbad, B. L.; Nile, S. H. Eur. J. Med. Chem. 2010, 45(6), 2629. doi: 10.1016/j.ejmech.2010.01.050
11. [11]
  La, M. I.; Jun, K. I.; Jhun KR 20140016848, 2014.
12. [12]
  Li, W. W.; Zhao, Y. P.; Xu, X. L. FEBS J. 2015, 282(12), 2317. doi: 10.1111/febs.13278
13. [13]
  Moon, S. J.; Park, J. S.; Woo, Y. J. Arthritis Rheumatol. 2014, 66(4), 874.
14. [14]
  Cho, E. H.; Choi, S. J.; Lee, S. W. EP2987491, 2016.
15. [15]
  Li, X. M.; Zhao, M.; Tang, Y. R. Eur. J. Med. Chem. 2008, 43(1), 8. doi: 10.1016/j.ejmech.2007.03.015
16. [16]
  Leite, A. C. L.; Barbosa, F. F.; Moreira, D. R. M. Med. Chem. Res. 2013, 23(4), 1701.
17. [17]
  Papadakis, K. A.; Targan, S. R. Annu. Rev. Med. 2000, 51(1), 289. doi: 10.1146/annurev.med.51.1.289
18. [18]
  Uchida, M.; Tabusa, F.; Komatsu, M.; Morita, S.; Kanbe, T.; Nakagawa, K. Chem. Pharm. Bull. 1986, 34, 4821. doi: 10.1248/cpb.34.4821
19. [19]
  Bashiardes, G.; Safir, I.; Barbot, F. Synlett 2007, 1707.
1. [1]
  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
2. [2]
  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
3. [3]
  Weiwei Liu , Yu Liu , Zhaoyan Tian , Zhaohan Wang , Hui Liu , Songqin Liu , Yafeng Wu . Online detecting living cells released TNF-α and studying intercellular communication using SuperDNA self-assembled conical nanochannel. Chinese Chemical Letters, 2025, 36(5): 110561-. doi: 10.1016/j.cclet.2024.110561
4. [4]
  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
5. [5]
  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
6. [6]
  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
7. [7]
  Lixing ZHANG , Yaowen WANG , Xu HAN , Junhong ZHOU , Jinghui WANG , Liping LI , Guangshe LI . Research progress in the synthesis of fluorine-containing perovskites and their derivatives. Chinese Journal of Inorganic Chemistry, 2025, 41(9): 1689-1701. doi: 10.11862/CJIC.20250007
8. [8]
  Wenyi Mei , Lijuan Xie , Xiaodong Zhang , Cunjian Shi , Fengzhi Wang , Qiqi Fu , Zhenjiang Zhao , Honglin Li , Yufang Xu , Zhuo Chen . Design, synthesis and biological evaluation of fluorescent derivatives of ursolic acid in living cells. Chinese Chemical Letters, 2024, 35(5): 108825-. doi: 10.1016/j.cclet.2023.108825
9. [9]
  Anqiu LIU , Long LIN , Dezhi ZHANG , Junyu LEI , Kefeng WANG , Wei ZHANG , Junpeng ZHUANG , Haijun HAO . Synthesis, structures, and catalytic activity of aluminum and zinc complexes chelated by 2-((2,6-dimethylphenyl)amino)ethanolate. Chinese Journal of Inorganic Chemistry, 2024, 40(4): 791-798. doi: 10.11862/CJIC.20230424
10. [10]
  Xiang Huang , Dongzhen Xu , Yang Liu , Xia Huang , Yangfan Wu , Dongmei Fang , Bing Xia , Wei Jiao , Jian Liao , Min Wang . Asymmetric synthesis of difluorinated α-quaternary amino acids (DFAAs) via Cu-catalyzed difluorobenzylation of aldimine esters. Chinese Chemical Letters, 2024, 35(12): 109665-. doi: 10.1016/j.cclet.2024.109665
11. [11]
  Min-Hang Zhou , Jun Jiang , Wei-Min He . EDA-complexes-enabled photochemical synthesis of α-amino acids with imines and tetrabutylammonium oxalate. Chinese Chemical Letters, 2025, 36(1): 110446-. doi: 10.1016/j.cclet.2024.110446
12. [12]
  Zhengzheng LIU , Pengyun ZHANG , Chengri WANG , Shengli HUANG , Guoyu YANG . Synthesis, structure, and electrochemical properties of a sandwich-type {Co₆}-cluster-added germanotungstate. Chinese Journal of Inorganic Chemistry, 2024, 40(6): 1173-1179. doi: 10.11862/CJIC.20240039
13. [13]
  Shuwen SUN , Gaofeng WANG . Design and synthesis of a Zn(Ⅱ)-based coordination polymer as a fluorescent probe for trace monitoring 2, 4, 6-trinitrophenol. Chinese Journal of Inorganic Chemistry, 2025, 41(4): 753-760. doi: 10.11862/CJIC.20240399
14. [14]
  Yulin Mao , Jingyu Ma , Jiecheng Ji , Yuliang Wang , Wanhua Wu , Cheng Yang . Crown aldoxime ethers: Their synthesis, structure, acid-catalyzed/photo-induced isomerization and adjustable guest binding. Chinese Chemical Letters, 2024, 35(11): 109927-. doi: 10.1016/j.cclet.2024.109927
15. [15]
  Guoping Yang , Zhoufu Lin , Xize Zhang , Jiawei Cao , Xuejiao Chen , Yufeng Liu , Xiaoling Lin , Ke Li . Assembly of Y(Ⅲ)-containing antimonotungstates induced by malic acid with catalytic activity for the synthesis of imidazoles. Chinese Chemical Letters, 2024, 35(12): 110274-. doi: 10.1016/j.cclet.2024.110274
16. [16]
  Dongdong YANG , Jianhua XUE , Yuanyu YANG , Meixia WU , Yujia BAI , Zongxuan WANG , Qi MA . Design and synthesis of two coordination polymers for the rapid detection of ciprofloxacin based on triphenylpolycarboxylic acid ligands. Chinese Journal of Inorganic Chemistry, 2024, 40(12): 2466-2474. doi: 10.11862/CJIC.20240266
17. [17]
  Jiajun Lu , Zhehui Liao , Tongxiang Cao , Shifa Zhu . Synergistic Brønsted/Lewis acid catalyzed atroposelective synthesis of aryl-β-naphthol. Chinese Chemical Letters, 2025, 36(1): 109842-. doi: 10.1016/j.cclet.2024.109842
18. [18]
  Jimin HOU , Mengyang LI , Chunhua GONG , Shaozhuang ZHANG , Caihong ZHAN , Hao XU , Jingli XIE . Synthesis, structures, and properties of metal-organic frameworks based on bipyridyl ligands and isophthalic acid. Chinese Journal of Inorganic Chemistry, 2025, 41(3): 549-560. doi: 10.11862/CJIC.20240348
19. [19]
  Nana Yang , Rui Yuan , Xinyue Fu , Xiao Tian , Jin Yu , Shengzhou Ma , Liuqing Wen , Jiabin Zhang . Concise synthesis of NDP-activated uronic acid by an oxidation reaction insertion strategy. Chinese Chemical Letters, 2025, 36(8): 110757-. doi: 10.1016/j.cclet.2024.110757
20. [20]
  Meijuan Chen , Liyun Zhao , Xianjin Shi , Wei Wang , Yu Huang , Lijuan Fu , Lijun Ma . Synthesis of carbon quantum dots decorating Bi₂MoO₆ microspherical heterostructure and its efficient photocatalytic degradation of antibiotic norfloxacin. Chinese Chemical Letters, 2024, 35(8): 109336-. doi: 10.1016/j.cclet.2023.109336

Get Citation

PDF

XML

Metrics

PDF Downloads(6)
Abstract views(774)
HTML views(47)

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