Synthesis, DNA binding and cytotoxic evaluation of aminoquinoline scaffolds

被引:7
|
作者
Kumar, Gopal Senthil [1 ]
Ali, Mohamed Ashraf [2 ,3 ,4 ]
Choon, Tan Soo [2 ]
Prasad, Karnam Jayarampillai Rajendra [1 ]
机构
[1] Bharathiar Univ, Dept Chem, Coimbatore 641046, Tamil Nadu, India
[2] Univ Sains Malaysia, Inst Res Mol Med, Minden 11800, Penang, Malaysia
[3] Alwar Pharm Coll, Dept Med Chem, New Drug Discovery Res, Alwar 301030, Rajasthan, India
[4] Sunrise Univ, Dept Med Chem, New Drug Discovery Res, Alwar 301030, Rajasthan, India
关键词
Hydrazinylquinolines; Isoindolin-1,3-diones; DNA binding; cytotoxicity; ANTITUMOR-ACTIVITY; PHTHALIMIDE; CHLOROQUINE; DERIVATIVES; QUINOLINES; GROWTH; DRUG;
D O I
10.1007/s12039-015-1025-5
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
An effortless synthetic route has been developed for the synthesis of a new class of aminoquinoline substituted isoindolin-1,3-diones from regio-isomerical hydrazinylquinolines with phthalic anhydride in presence of Eaton's reagent. DNA binding studies of selected isomeric compounds showed interaction with DNA via intercalation mode with higher binding affinity of 4-substituted quinolines rather than 2-substituted counterparts. Further, all compounds were screened for cytotoxic activity against three human cancer cell lines, among them compound 2c outranged standard doxorubicin against CCRF-CEM cell line.
引用
收藏
页码:391 / 400
页数:10
相关论文
共 50 条
  • [1] Synthesis, DNA binding and cytotoxic evaluation of aminoquinoline scaffolds
    GOPAL SENTHIL KUMAR
    MOHAMED ASHRAF ALI
    TAN SOO CHOON
    KARNAM JAYARAMPILLAI RAJENDRA PRASAD
    Journal of Chemical Sciences, 2016, 128 : 391 - 400
  • [2] Synthesis of diphenylcarbazoles as cytotoxic DNA binding agents
    Jacquemard, U
    Routier, S
    Tatibouët, A
    Kluza, J
    Laine, W
    Bal, C
    Bailly, C
    Mérour, JY
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2004, 2 (10) : 1476 - 1483
  • [3] Synthesis, DNA binding, and cytotoxic evaluation of new analogs of diallyldisulfide, an active principle of garlic
    Rai, Santosh Kumar
    Sharma, Meenakshi
    Tiwari, Manisha
    BIOORGANIC & MEDICINAL CHEMISTRY, 2008, 16 (15) : 7301 - 7309
  • [4] BINDING OF 8-AMINOQUINOLINE ANTIMALARIALS TO DNA
    MORRIS, CR
    WHICHARD, LP
    HOLBROOK, DJ
    FEDERATION PROCEEDINGS, 1968, 27 (02) : 713 - &
  • [5] Synthesis, characterization, antiparasitic and cytotoxic evaluation of thioureas conjugated to polyamine scaffolds
    Stringer, Tameryn
    Taylor, Dale
    de Kock, Carmen
    Guzgay, Hajira
    Au, Aaron
    An, Seung Hwan
    Sanchez, Benjamin
    O'Connor, Raquel
    Patel, Neal
    Land, Kirkwood M.
    Smith, Peter J.
    Hendricks, Denver T.
    Egan, Timothy J.
    Smith, Gregory S.
    EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2013, 69 : 90 - 98
  • [6] Synthesis, cytotoxic activities and DNA binding properties of β-carboline derivatives
    Chen, Zhiyong
    Cao, Rihui
    Yu, Liang
    Shi, Buxi
    Sun, Jie
    Guo, Liang
    Ma, Qin
    Yi, Wei
    Song, Xiao
    Song, Huacan
    EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2010, 45 (11) : 4740 - 4745
  • [7] Synthesis, DNA-binding, molecular docking and cytotoxic activity in vitro evaluation of ruthenium(II) complexes
    Huang, Hong-Liang
    Tang, Bing
    Yi, Qiao-Yan
    Wan, Dan
    Yang, Lin-Lin
    Liu, Yun-Jun
    TRANSITION METAL CHEMISTRY, 2019, 44 (01) : 11 - 24
  • [8] New binuclear Cu (II) complex: synthesis, structural elucidation, cytotoxic and DNA-binding evaluation
    Mouayed A. Hussein
    Adyan A. Yaseen
    Transition Metal Chemistry, 2024, 49 : 53 - 62
  • [9] Synthesis, DNA-binding, molecular docking and cytotoxic activity in vitro evaluation of ruthenium(II) complexes
    Hong-Liang Huang
    Bing Tang
    Qiao-Yan Yi
    Dan Wan
    Lin-Lin Yang
    Yun-Jun Liu
    Transition Metal Chemistry, 2019, 44 : 11 - 24
  • [10] New binuclear Cu (II) complex: synthesis, structural elucidation, cytotoxic and DNA-binding evaluation
    Hussein, Mouayed A.
    Yaseen, Adyan A.
    TRANSITION METAL CHEMISTRY, 2024, 49 (01) : 53 - 62