Graphene oxide as an active carbocatalyst for cyanation of quinoline and isoquinoline N-Oxides

被引:1
|
作者
Huang, Panpan [1 ]
Peng, Xiangjun [2 ]
Qiu, Genhong [2 ]
Yu, Keyang [2 ]
Li, Hong [1 ]
Kong, Lingting [1 ]
Hu, Jiaming [1 ]
Chen, Zhengwang [1 ]
Huang, Qing [1 ]
Liu, Liangxian [1 ]
机构
[1] Gannan Normal Univ, Dept Chem & Chem Engn, Ganzhou 341000, Jiangxi, Peoples R China
[2] Gannan Med Univ, Sch Pharmaceut Sci, Ganzhou 341000, Jiangxi, Peoples R China
基金
中国国家自然科学基金;
关键词
Graphene oxide; Heterocyclic N-Oxides; (Iso)quinoline; Nitrile;
D O I
10.1016/j.tet.2021.131964
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Graphene oxide was found to be a highly efficient and cost-effective heterogeneous catalyst for the direct metal-free transformation of quinoline and isoquinoline N-oxides into the corresponding nitriles under mild conditions. This method is simple, economic and environmentally benign, representing a useful strategy for the convenient synthesis of alpha-cyano N-oxides that are difficult to prepare by transition-metal-free catalyzed methods. In vitro, compound 2s exhibited good activities against T-24 cell lines with IC50 values in 10.23 +/- 1.05 mu M. Further studies investigated the mechanism of the effective inhibition of cell growth, including apoptosis ratio dection, cell cycle analysis, measurement of Ca2+ generation, ROS, and mitochondrial dysfunction. (C) 2021 Elsevier Ltd. All rights reserved.
引用
收藏
页数:7
相关论文
共 11 条
  • [1] Gold-Catalyzed Redox-Neutral Reaction of Nitriles with Quinoline N-Oxides
    Wu, Jiawen
    Xia, Zhonghua
    ADVANCED SYNTHESIS & CATALYSIS, 2023, 365 (19) : 3335 - 3341
  • [2] Bronsted Acidic Ionic Liquid-Promoted Amidation of Quinoline N-Oxides with Nitriles
    Xie, Long-Yong
    Peng, Sha
    Lu, Ling-Hui
    Hu, Jue
    Bao, Wen-Hu
    Zeng, Fei
    Tang, Zilong
    Xu, Xinhua
    He, Wei-Min
    ACS SUSTAINABLE CHEMISTRY & ENGINEERING, 2018, 6 (06): : 7989 - 7994
  • [3] N-formylation of amine using graphene oxide as a sole recyclable metal-free carbocatalyst
    Ma, Juan
    Zhang, Jingyu
    Zhou, Xiao
    Wang, Jiawei
    Gong, Hang
    JOURNAL OF THE IRANIAN CHEMICAL SOCIETY, 2018, 15 (12) : 2851 - 2860
  • [4] N-formylation of amine using graphene oxide as a sole recyclable metal-free carbocatalyst
    Juan Ma
    Jingyu Zhang
    Xiao Zhou
    Jiawei Wang
    Hang Gong
    Journal of the Iranian Chemical Society, 2018, 15 : 2851 - 2860
  • [5] Metal-free Deoxygenative 2-Amidation of Quinoline N-oxides with Nitriles via a Radical Activation Pathway
    Xie, Long-Yong
    Peng, Sha
    Liu, Fang
    Yi, Jin-Yu
    Wang, Ming
    Tang, Zilong
    Xu, Xinhua
    He, Wei-Min
    ADVANCED SYNTHESIS & CATALYSIS, 2018, 360 (21) : 4259 - 4264
  • [6] Sonochemically N-functionalized graphene oxide towards optically active photoluminescent bioscaffold
    Avashthi, Gopal
    Maktedar, Shrikant S.
    Singh, Man
    ULTRASONICS SONOCHEMISTRY, 2019, 58
  • [7] An N-Halamine/Graphene Oxide-Functionalized Electrospun Polymer Membrane That Inactivates Bacteria on Contact and by Releasing Active Chlorine
    Lan, Shi
    Zhang, Jinghua
    Li, Jie
    Guo, Yanan
    Sheng, Xianliang
    Dong, Alideertu
    POLYMERS, 2021, 13 (16)
  • [8] Highly Active and Stable Bis Imidazolium-Based Copper N-heterocyclic Carbene Modified Graphene Oxide for O-arylation and N-arylation Reactions in Water
    Morteza Imanpour
    Kamran Lamei
    Hossein Eshghi
    Catalysis Letters, 2023, 153 : 1390 - 1409
  • [9] Highly Active and Stable Bis Imidazolium-Based Copper N-heterocyclic Carbene Modified Graphene Oxide for O-arylation and N-arylation Reactions in Water
    Imanpour, Morteza
    Lamei, Kamran
    Eshghi, Hossein
    CATALYSIS LETTERS, 2023, 153 (05) : 1390 - 1409
  • [10] Ultrahigh peroxidase-like catalytic performance of Cu -N 4 and Cu -N 4 S active sites-containing reduced graphene oxide for sensitive electrochemical biosensing
    Le, Phan Gia
    Le, Xuan Ai
    Duong, Hai Sang
    Kim, Taeyoung
    Kim, Moon Il
    BIOSENSORS & BIOELECTRONICS, 2024, 255