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

被引:7
|
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
相关论文
共 50 条
  • [1] Enantioselective conjugate addition of 3-fluorooxindoles to vinyl sulfone: an organocatalytic access to chiral 3-fluoro-3-substituted oxindoles
    Dou, Xiaowei
    Lu, Yixin
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2013, 11 (32) : 5217 - 5221
  • [2] Synthesis of 3-substituted 3-fluoro-2-oxindoles by deacylative alkylation
    Molina, Cynthia
    Ortega-Martinez, Aitor
    Sansano, Jose M.
    Najera, Carmen
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2019, 17 (03) : 482 - 489
  • [3] SUBSTITUTED OXINDOLES .3. SYNTHESIS AND PHARMACOLOGY FO SOME SUBSTITUTED OXINDOLES
    WALKER, J
    DAISLEY, RW
    BECKETT, AH
    JOURNAL OF MEDICINAL CHEMISTRY, 1970, 13 (05) : 983 - &
  • [4] Synthesis of 3-Fluoro-3-aryl Oxindoles: Direct Enantioselective a Arylation of Amides
    Wu, Linglin
    Falivene, Laura
    Drinkel, Emma
    Grant, Sharday
    Linden, Anthony
    Cavallo, Luigi
    Dorta, Reto
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2012, 51 (12) : 2870 - 2873
  • [5] Enantioselective synthesis of 3-fluoro-3-allyl-oxindoles via phosphine-catalyzed asymmetric γ-addition of 3-fluoro-oxindoles to 2,3-butadienoates
    Wang, Tianli
    Hoon, Ding Long
    Lu, Yixin
    CHEMICAL COMMUNICATIONS, 2015, 51 (50) : 10186 - 10189
  • [6] New synthesis of 3-aryl substituted oxindoles.
    Ly, TM
    Laso, NM
    Zard, SZ
    TETRAHEDRON, 1998, 54 (19) : 4889 - 4898
  • [7] Stereochemical implications in the synthesis of 3,3′-spirocyclopropyl oxindoles from β-aryl/alkyl-substituted alkylidene oxindoles
    Wilson, Erin E.
    Rodriguez, Kevin X.
    Ashfeld, Brandon L.
    TETRAHEDRON, 2015, 71 (35) : 5765 - 5775
  • [8] Catalytic Asymmetric Synthesis of Substituted 3-Hydroxy-2-Oxindoles
    Hanhan, Nadine V.
    Sahin, Aziza H.
    Chang, Toby W.
    Fettinger, James C.
    Franz, Annaliese K.
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2010, 49 (04) : 744 - 747
  • [9] A Facile Method for the Synthesis of 3-Substituted 3-(Alkylthio)oxindoles or 3-Alkoxyoxindoles
    Zhu, Feng
    Zhou, Feng
    Cao, Zhong-Yan
    Wang, Chao
    Zhang, Yong-Xue
    Wang, Cui-Hong
    Zhou, Jian
    SYNTHESIS-STUTTGART, 2012, 44 (20): : 3129 - 3144
  • [10] A new Claisen sequence for the synthesis of 3-substituted-2-oxindoles
    Booker-Milburn, KI
    Fedouloff, M
    Paknoham, SJ
    Strachan, JB
    Melville, JL
    Voyle, M
    TETRAHEDRON LETTERS, 2000, 41 (23) : 4657 - 4661