Citation: Huang Erfang, Zhang Lan, Xiao Chuying, Meng Guangpeng, Zhang Bingqi, Hu Jianshu, Wan David Chi-Cheong, Meng Qingguo, Jin Zhe, Hu Chun. Synthesis and biological evaluation of indole-3-carboxamide derivatives as antioxidant agents[J]. Chinese Chemical Letters, ;2019, 30(12): 2157-2159. doi: 10.1016/j.cclet.2019.04.044 shu

Synthesis and biological evaluation of indole-3-carboxamide derivatives as antioxidant agents

a.
Key Laboratory of Structure-based Drug Design & Discovery, Ministry of Education, Shenyang Pharmaceutical University, Shenyang 110016, China
b.
School of Biomedical Sciences, Faculty of Medicine, The Chinese University of Hong Kong, Hong Kong, China
c.
Department of Pharmacy, Yantai Univeristy, Yantai 264005, China

jinzheln@163.com

chunhu1999@163.com

Received Date: 27 February 2019
Revised Date: 15 April 2019
Accepted Date: 16 April 2019
Available Online: 17 December 2019

Figures(3)

Oxidative stress results in various pathologies and as consequence antioxidant agents have attracted uninterrupted attention. In this paper, a novel series of indole-3-carboxamide derivatives (6a-6l) were designed and synthesized based on the melatonin structure as novel antioxidants. All of them were evaluated for the antioxidant activities in vitro against human neuroblastoma SH-SY5Y cell line using H₂O₂ radical scavenging assay. The target compounds 6a, 6f and 6i indicated better activities than the positive control, ascorbic acid, and 6a exhibited the best antioxidant activity. In addition, the structureactivity relationships of the target compounds were also preliminarily summarized based on the obtained experimental data.
- Heterocycle,
- Melatonin,
- Indole-3-carboxamide derivatives,
- Synthesis,
- Antioxidant activity,
- Structure-activity relationship
1. [1]
  D. Lee, K.Y. Ry, Biochem. Biophys. Res. Commun. 485 (2017) 234-240. doi: 10.1016/j.bbrc.2017.02.105
2. [2]
  L. Zuo, T. Zhou, B.K. Pannell, A.C. Ziegler, T.M. Best, Acta Physiol. Oxf. (Oxf) 214 (2015) 329-348. doi: 10.1111/apha.12515
3. [3]
  J.I. Pagel, E. Deindl, Int. J. Mol. Sci. 13 (2012) 13104-13117. doi: 10.3390/ijms131013104
4. [4]
  C. Hoelzl, J. Bichler, F. Ferk, et al., J. Physiol. Pharmacol. 56 (2005) 49-64.
5. [5]
  H.L. Wang, Z.Y. Yang, B.D. Wang, Transit. Metal Chem. 31 (2006) 470-474. doi: 10.1007/s11243-006-0015-3
6. [6]
  Y. Zhang, B. Zou, Z. Chen, et al., Bioorg. Med. Chem. Lett. 21 (2011) 6811-6815. doi: 10.1016/j.bmcl.2011.09.029
7. [7]
  F. Rostami-Charati, Chin. Chem. Lett. 25 (2014) 169-171. doi: 10.1016/j.cclet.2013.09.016
8. [8]
  M. Mor, C. Silva, F. Vacondio, et al., J. Pineal Res. 36 (2004) 95-102. doi: 10.1046/j.1600-079X.2003.00102.x
9. [9]
  M. Karbownik, E. Gitto, A. Lewiñski, R.J. Reiter, J. Cell. Biochem. 81 (2001) 693-699. doi: 10.1002/jcb.1100
10. [10]
  C. Phiphatwatcharaded, P. Puthongking, P. Chaiyarit, et al., Arch. Oral Biol. 9 (2017) 55-61.
11. [11]
  D. Bonnefont-Rousselot, F. Collin, Toxicology 278 (2010) 55-67. doi: 10.1016/j.tox.2010.04.008
12. [12]
  Y. Guney, A. Hicsonmez, C. Uluoglu, et al., Braz. J. Med. Biol. Res. 40 (2007) 1305-1314. doi: 10.1590/S0100-879X2006005000156
13. [13]
  S. Cuesta, R. Kireev, C. García, et al., Mech. Ageing Dev. 132 (2011) 573-582. doi: 10.1016/j.mad.2011.10.005
14. [14]
  F. Radogna, M. Diederich, L. Ghibelli, Biochem. Pharmacol. 80 (2010) 1844-1852. doi: 10.1016/j.bcp.2010.07.041
15. [15]
  A. Maheshwari, M.M. Misro, A. Aggarwal, R.K. Sharma, D. Nandan, FEBS J. 276 (2009) 870-881. doi: 10.1111/j.1742-4658.2008.06831.x
16. [16]
  K.X. Huang, Y.B. Feng, W. Yao, et al., Chin. Chem. Lett. 20 (2009) 1187-1190. doi: 10.1016/j.cclet.2009.04.026
17. [17]
  J.D. Xu, L.W. Zhang, Y.F. Liu, Chin. Chem. Lett. 24 (2013) 223-226. doi: 10.1016/j.cclet.2013.01.016
1. [1]
  Yulong Shi , Fenbei Chen , Mengyuan Wu , Xin Zhang , Runze Meng , Kun Wang , Yan Wang , Yuheng Mei , Qionglu Duan , Yinghong Li , Rongmei Gao , Yuhuan Li , Hongbin Deng , Jiandong Jiang , Yanxiang Wang , Danqing Song . Chemical construction and anti-HCoV-OC43 evaluation of novel 10,12-disubstituted aloperine derivatives as dual cofactor inhibitors of TMPRSS2 and SR-B1. Chinese Chemical Letters, 2024, 35(5): 108792-. doi: 10.1016/j.cclet.2023.108792
2. [2]
  Huiju Cao , Lei Shi . sp¹-Hybridized linear and cyclic carbon chain. Chinese Chemical Letters, 2025, 36(4): 110466-. doi: 10.1016/j.cclet.2024.110466
3. [3]
  Qin Cheng , Ming Huang , Qingqing Ye , Bangwei Deng , Fan Dong . Indium-based electrocatalysts for CO₂ reduction to C1 products. Chinese Chemical Letters, 2024, 35(6): 109112-. doi: 10.1016/j.cclet.2023.109112
4. [4]
  A-Yang Wang , Sheng-Hua Zhou , Mao-Yin Ran , Xin-Tao Wu , Hua Lin , Qi-Long Zhu . Regulating the key performance parameters for Hg-based IR NLO chalcogenides via bandgap engineering strategy. Chinese Chemical Letters, 2024, 35(10): 109377-. doi: 10.1016/j.cclet.2023.109377
5. [5]
  Anjing Liao , Wei Sun , Yaming Liu , Han Yan , Zhi Xia , Jian Wu . Pyrrole and pyrrolidine analogs: The promising scaffold in discovery of pesticides. Chinese Chemical Letters, 2025, 36(3): 110094-. doi: 10.1016/j.cclet.2024.110094
6. [6]
  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
7. [7]
  Jian Song , Shenghui Wang , Qiuge Liu , Xiao Wang , Shuo Yuan , Hongmin Liu , Saiyang Zhang . N-Benzyl arylamide derivatives as novel and potent tubulin polymerization inhibitors against gastric cancers: Design, structure–activity relationships and biological evaluations. Chinese Chemical Letters, 2025, 36(2): 109678-. doi: 10.1016/j.cclet.2024.109678
8. [8]
  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
9. [9]
  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
10. [10]
  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
11. [11]
  Maitri Bhattacharjee , Rekha Boruah Smriti , R. N. Dutta Purkayastha , Waldemar Maniukiewicz , Shubhamoy Chowdhury , Debasish Maiti , Tamanna Akhtar . Synthesis, structural characterization, bio-activity, and density functional theory calculation on Cu(Ⅱ) complexes with hydrazone-based Schiff base ligands. Chinese Journal of Inorganic Chemistry, 2024, 40(7): 1409-1422. doi: 10.11862/CJIC.20240007
12. [12]
  Xiaomeng Hu , Jie Yu , Lijie Sun , Linfeng Zhang , Wei Zhou , Dongpeng Yan , Xinrui Wang . Synthesis of an AVB@ZnTi-LDH composite with synergistically enhance UV blocking activity and high stability for potential application in sunscreen formulations. Chinese Chemical Letters, 2024, 35(11): 109466-. doi: 10.1016/j.cclet.2023.109466
13. [13]
  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
14. [14]
  Ping Sun , Yuanqin Huang , Shunhong Chen , Xining Ma , Zhaokai Yang , Jian Wu . Indole derivatives as agrochemicals: An overview. Chinese Chemical Letters, 2024, 35(7): 109005-. doi: 10.1016/j.cclet.2023.109005
15. [15]
  Xinyu Tian , Jiaxiang Guo , Zeyi Li , Shihou Sheng , Tianyu Zhang , Xianfei Li , Chuandong Dou . Control over electronic structures of organic diradicaloids via precise B/O-heterocycle fusion. Chinese Chemical Letters, 2025, 36(1): 110174-. doi: 10.1016/j.cclet.2024.110174
16. [16]
  Guangyao Wang , Zhitong Xu , Ye Qi , Yueguang Fang , Guiling Ning , Junwei Ye . Electrospun nanofibrous membranes with antimicrobial activity for air filtration. Chinese Chemical Letters, 2024, 35(10): 109503-. doi: 10.1016/j.cclet.2024.109503
17. [17]
  Ya-Nan Yang , Zi-Sheng Li , Sourav Mondal , Lei Qiao , Cui-Cui Wang , Wen-Juan Tian , Zhong-Ming Sun , John E. McGrady . Metal-metal bonds in Zintl clusters: Synthesis, structure and bonding in [Fe₂Sn₄Bi₈]^3– and [Cr₂Sb₁₂]^3–. Chinese Chemical Letters, 2024, 35(8): 109048-. doi: 10.1016/j.cclet.2023.109048
18. [18]
  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
19. [19]
  Teng-Yu Huang , Junliang Sun , De-Xian Wang , Qi-Qiang Wang . Recent progress in chiral zeolites: Structure, synthesis, characterization and applications. Chinese Chemical Letters, 2024, 35(12): 109758-. doi: 10.1016/j.cclet.2024.109758
20. [20]
  Ao Sun , Zipeng Li , Shuchun Li , Xiangbao Meng , Zhongtang Li , Zhongjun Li . Stereoselective synthesis of α-3-deoxy-D-manno-oct-2-ulosonic acid (α-Kdo) derivatives using a C3-p-tolylthio-substituted Kdo fluoride donor. Chinese Chemical Letters, 2025, 36(3): 109972-. doi: 10.1016/j.cclet.2024.109972

Get Citation

PDF

XML

Metrics

PDF Downloads(4)
Abstract views(620)
HTML views(9)

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