Design, synthesis and insilico studies of 3-fluoro-3-substituted oxindoles against cancer targets

被引:8
作者
Ranganath, P. L. N. [1 ,2 ]
Narsaiah, Venkat [1 ,2 ]
机构
[1] Indian Inst Chem Technol, Fluoro Agrochem Dept, Organ Synth Lab, CSIR, ,, Hyderabad 500007, Telangana, India
[2] Acad Sci & Innovat Res AcSIR, Ghaziabad 201002, India
关键词
Isatin; Aldol reaction; Fluorination; Insilico studies; Anti; -cancer; FLUORINE;
D O I
10.1016/j.jfluchem.2023.110134
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
Isatin and substituted isatins were subjected to Aldol condensation with various ketones. The resulted 3-hydroxy compounds were transformed into fluorine derivatives. Thus obtained, 3-fluoro-3-substituted oxindoles were screened for Insilco evaluation against anti-cancer targets VEGFR2 and GSK-3 beta. The study reveals that the fluoro compounds showed binding at their active sites. Particularly, compounds 4i, 4n and 4q shows the best binding affinity and similar hydrophobic interactions as their respective co-crystallized ligands.
引用
收藏
页数:11
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共 26 条
  • [1] [Anonymous], 2017, GLID VERS 7 1
  • [2] [Anonymous], 2017, MAESTR VERS 11 2
  • [3] Structural characterization of the GSK-3β active site using selective and non-selective ATP-mimetic inhibitors
    Bertrand, JA
    Thieffine, S
    Vulpetti, A
    Cristiani, C
    Valsasina, B
    Knapp, S
    Kalisz, HM
    Flocco, M
    [J]. JOURNAL OF MOLECULAR BIOLOGY, 2003, 333 (02) : 393 - 407
  • [4] Hit optimization studies of 3-hydroxy-indolin-2-one analogs as potential anti-HIV-1 agents
    Chander, Subhash
    Tang, Cheng-Run
    Penta, Ashok
    Wang, Ping
    Bhagwat, Deepak P.
    Vanthuyne, Nicolas
    Albalat, Muriel
    Patel, Payal
    Sankpal, Sanskruti
    Zheng, Yong-Tang
    Sankaranarayanan, Murugesan
    [J]. BIOORGANIC CHEMISTRY, 2018, 79 : 212 - 222
  • [5] Therapeutic Outcomes of Isatin and Its Derivatives against Multiple Diseases: Recent Developments in Drug Discovery
    Cheke, Rameshwar S.
    Patil, Vaishali M.
    Firke, Sandip D.
    Ambhore, Jaya P.
    Ansari, Iqrar A.
    Patel, Harun M.
    Shinde, Sachin D.
    Pasupuleti, Visweswara Rao
    Hassan, Md Imtaiyaz
    Adnan, Mohd
    Kadri, Adel
    Snoussi, Mejdi
    [J]. PHARMACEUTICALS, 2022, 15 (03)
  • [6] Clayden J, 2019, NATURE, V573, P37, DOI 10.1038/d41586-019-02611-7
  • [7] Anticancer Compounds Based on Isatin-Derivatives: Strategies to Ameliorate Selectivity and Efficiency
    Ferraz de Paiva, Raphael Enoque
    Vieira, Eduardo Guimaraes
    Rodrigues da Silva, Daniel
    Wegermann, Camila Anchau
    Costa Ferreira, Ana Maria
    [J]. FRONTIERS IN MOLECULAR BIOSCIENCES, 2021, 7
  • [8] Chemical Aspects of Human and Environmental Overload with Fluorine
    Han, Jianlin
    Kiss, Lorand
    Mei, Haibo
    Remete, Attila Mario
    Ponikvar-Svet, Maja
    Sedgwick, Daniel Mark
    Roman, Raquel
    Fustero, Santos
    Moriwaki, Hiroki
    Soloshonok, Vadim A.
    [J]. CHEMICAL REVIEWS, 2021, 121 (08) : 4678 - 4742
  • [9] Next generation organofluorine containing blockbuster drugs
    Han, Jianlin
    Remete, Attila Mario
    Dobson, Luca S.
    Kiss, Lorand
    Izawa, Kunisuke
    Moriwaki, Hiroki
    Soloshonok, Vadim A.
    O'Hagan, David
    [J]. JOURNAL OF FLUORINE CHEMISTRY, 2020, 239
  • [10] Fluorine-containing drugs approved by the FDA in 2021
    He, Jingrui
    Li, Ziyi
    Dhawan, Gagan
    Zhang, Wei
    Sorochinsky, Alexander E.
    Butler, Greg
    Soloshonok, Vadim A.
    Han, Jianlin
    [J]. CHINESE CHEMICAL LETTERS, 2023, 34 (01)