Solvent effect on copper-catalyzed azide-alkyne cycloaddition (CuAAC): Synthesis of novel triazolyl substituted quinolines as potential anticancer agents

被引:26
|
作者
Ellanki, Amarender Reddy [2 ,5 ]
Islam, Aminul [2 ]
Rama, Veera Swamy [2 ]
Pulipati, Ranga Prasad [2 ]
Rambabu, D. [1 ,3 ]
Krishna, G. Rama [4 ]
Reddy, C. Malla [4 ]
Mukkanti, K. [5 ]
Vanaja, G. R. [6 ]
Kalle, Arunasree M. [6 ]
Kumar, K. Shiva [1 ]
Pal, Manojit [1 ]
机构
[1] Inst Life Sci, Hyderabad 500046, Andhra Pradesh, India
[2] Dr Reddys Labs Ltd, Chem Technol Dev Ctr, Hyderabad 500049, Andhra Pradesh, India
[3] KL Univ, Dept Chem, Guntur 522502, Andhra Pradesh, India
[4] Indian Inst Sci Educ & Res, Dept Chem Sci, Kolkata 741252, W Bengal, India
[5] JNT Univ, Inst Sci & Technol, Div Chem, Hyderabad 500072, Andhra Pradesh, India
[6] Univ Hyderabad, Sch Life Sci, Dept Anim Sci, Hyderabad 500046, Andhra Pradesh, India
关键词
Click chemistry; Azide; Alkyne; Quinoline; Cancer; CLICK CHEMISTRY; 1,3-DIPOLAR CYCLOADDITIONS; EFFICIENT;
D O I
10.1016/j.bmcl.2012.03.091
中图分类号
R914 [药物化学];
学科分类号
100701 ;
摘要
A regioselective route to novel mono triazolyl substituted quinolines has been developed via copper-catalyzed azide-alkyne cycloaddition (CuAAC) of 2,4-diazidoquinoline with terminal alkynes in DMF. The reaction provided bis triazolyl substituted quinolines when performed in water in the presence of Et3N. A number of the compounds synthesized showed promising anti-proliferative properties when tested in vitro especially against breast cancer cells. (C) 2012 Elsevier Ltd. All rights reserved.
引用
收藏
页码:3455 / 3459
页数:5
相关论文
共 50 条
  • [1] Development and Applications of the Copper-Catalyzed Azide-Alkyne Cycloaddition (CuAAC) as a Bioorthogonal Reaction
    Li, Li
    Zhang, Zhiyuan
    MOLECULES, 2016, 21 (10)
  • [2] Recent Advances in Recoverable Systems for the Copper-Catalyzed Azide-Alkyne Cycloaddition Reaction (CuAAC)
    Mandoli, Alessandro
    MOLECULES, 2016, 21 (09):
  • [3] Mechanistic Insights into Copper-Catalyzed Azide-Alkyne Cycloaddition (CuAAC): Observation of Asymmetric Amplification
    Osako, Takao
    Uozumi, Yasuhiro
    SYNLETT, 2015, 26 (11) : 1475 - 1479
  • [4] Copper-catalyzed azide-alkyne cycloaddition (CuAAC) and beyond: new reactivity of copper(I) acetylides
    Hein, Jason E.
    Fokin, Valery V.
    CHEMICAL SOCIETY REVIEWS, 2010, 39 (04) : 1302 - 1315
  • [5] Chalcones and Chromones in Copper-catalyzed Azide-Alkyne Cycloadditions (CuAAC)
    Tome, Sara M.
    Tome, Augusto C.
    Soengas, Raquel G.
    Silva, Artur M. S.
    CURRENT ORGANIC CHEMISTRY, 2018, 22 (13) : 1307 - 1325
  • [6] Kinetic resolution by copper-catalyzed azide-alkyne cycloaddition
    Meng, JC
    Fokin, VV
    Finn, MG
    TETRAHEDRON LETTERS, 2005, 46 (27) : 4543 - 4546
  • [7] Evaluation of biofilm formation on novel copper-catalyzed azide-alkyne cycloaddition (CuAAC)-based resins for dental restoratives
    Zajdowicz, Sheryl
    Song, Han Byul
    Baranek, Austin
    Bowman, Christopher N.
    DENTAL MATERIALS, 2018, 34 (04) : 657 - 666
  • [8] Photoinitiated copper(I) catalyzed azide-alkyne cycloaddition (CuAAC) reaction for conductive network synthesis
    El-Zaatari, Bassil
    Tibbits, Andrew
    Kloxin, Christopher
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2018, 255
  • [9] Copper-catalyzed Azide-alkyne Cycloaddition (CuAAC)-mediated Macrocyclization of Peptides: Impact on Conformation and Biological Activity
    Testa, Chiara
    Papini, Anna Maria
    Chorev, Michael
    Rovero, Paolo
    CURRENT TOPICS IN MEDICINAL CHEMISTRY, 2018, 18 (07) : 591 - 610
  • [10] Peptide cyclodimerization by copper-catalyzed azide-alkyne cycloaddition.
    Punna, S
    Kuzelka, J
    Wang, Q
    Finn, MG
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2005, 229 : U387 - U387