Literature DB >> 22119131

Synthesis and QSAR study of novel cytotoxic spiro[3H-indole-3,2'(1'H)-pyrrolo[3,4-c]pyrrole]-2,3',5'(1H,2'aH,4'H)-triones.

Adel S Girgis1, Jacek Stawinski, Nasser S M Ismail, Hanaa Farag.   

Abstract

1,3-Dipolar cycloaddition reaction of 1-aryl-1H-pyrrole-2,5-diones 1a-e with non-stabilized azomethine ylides, generated in situ via decarboxylative condensation of isatins 2a-c and sarcosine (3) in refluxing ethanol, afforded 4'-aryl-5'a,6'-dihydro-1'-methyl-spiro[3H-indole-3,2'(1'H)-pyrrolo[3,4-c]pyrrole]-2,3',5'(1H,2'aH,4'H)-triones 4a-o in good yields. Compound 4l exhibited high anti-tumor activity against HEPG2 (liver cancer) cell line (IC(50) = 12.16 μM) compared to that of Doxorubicin (IC(50) = 7.36 μM), and the other synthesized compounds revealed moderate anti-tumor properties against HCT116 (colon), MCF7 (breast) and HEPG2 (liver) human tumor cell lines. 3D-Pharmacophore modeling and quantitative structure-activity relationship (QSAR) analysis were combined to explore the structural requirements controlling the observed anti-tumor properties. It was found that the major structural factors affecting potency of these compounds were related to their basic skeleton.
Copyright © 2011 Elsevier Masson SAS. All rights reserved.

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Year:  2011        PMID： 22119131     DOI： 10.1016/j.ejmech.2011.10.058

Source DB:  PubMed          Journal:  Eur J Med Chem        ISSN： 0223-5234            Impact factor:   6.514


  12 in total

1.  A synthesis of fused acenaphthopyrrolizines via the 1,3-dipolar cycloaddition reaction of azomethine ylides with acetylenic esters.

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Journal:  Mol Divers       Date:  2017-01-13       Impact factor: 2.943

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Authors:  Ibrahim F Nassar; Mohammed T Abdel Aal; Wael A El-Sayed; Mahmoud A E Shahin; Elsayed G E Elsakka; Mahmoud Mohamed Mokhtar; Maghawry Hegazy; Mohamed Hagras; Asmaa A Mandour; Nasser S M Ismail
Journal:  RSC Adv       Date:  2022-05-17       Impact factor: 4.036

Review 3.  Molecular diversity of spirooxindoles. Synthesis and biological activity.

Authors:  Tetyana L Pavlovska; Ruslan Gr Redkin; Victoria V Lipson; Dmytro V Atamanuk
Journal:  Mol Divers       Date:  2015-09-29       Impact factor: 2.943

4.  5-Chloro-5''-(4-chloro-benzyl-idene)-4'-(4-chloro-phen-yl)-1',1''-dimethyldi-spiro-[indoline-3,2'-pyrrolidine-3',3''-piperidine]-2,4''-dione.

Authors:  I S Ahmed Farag; Adel S Girgis; A A Ramadan; A M Moustafa; Ahmed F Mabied
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2014-02-28

5.  The regioselective synthesis of spirooxindolo pyrrolidines and pyrrolizidines via three-component reactions of acrylamides and aroylacrylic acids with isatins and α-amino acids.

Authors:  Tatyana L Pavlovskaya; Fedor G Yaremenko; Victoria V Lipson; Svetlana V Shishkina; Oleg V Shishkin; Vladimir I Musatov; Alexander S Karpenko
Journal:  Beilstein J Org Chem       Date:  2014-01-09       Impact factor: 2.883

6.  A Facile One-Pot Construction of Succinimide-Fused Spiro[Pyrrolidine-2,3'-Oxindoles] via 1,3-Dipolar Cycloaddition Involving 3-Amino Oxindoles and Maleimides.

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Journal:  Molecules       Date:  2018-03-05       Impact factor: 4.411

7.  Design, synthesis and in silico studies of new quinazolinone derivatives as antitumor PARP-1 inhibitors.

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Journal:  RSC Adv       Date:  2020-08-10       Impact factor: 4.036

8.  1'-Methyl-4'-(4-methyl-phen-yl)dispiro-[indane-2,3'-pyrrolidine-2',3''-indoline]-1,2''-dione.

Authors:  A M Moustafa; Adel S Girgis; S M Shalaby; Edward R T Tiekink
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2012-06-23

9.  In Silico HCT116 Human Colon Cancer Cell-Based Models En Route to the Discovery of Lead-Like Anticancer Drugs.

Authors:  Sara Cruz; Sofia E Gomes; Pedro M Borralho; Cecília M P Rodrigues; Susana P Gaudêncio; Florbela Pereira
Journal:  Biomolecules       Date:  2018-07-17

10.  Discovery of New Pyrazolopyridine, Furopyridine, and Pyridine Derivatives as CDK2 Inhibitors: Design, Synthesis, Docking Studies, and Anti-Proliferative Activity.

Authors:  Adel A-H Abdel-Rahman; Amira K F Shaban; Ibrahim F Nassar; Dina S El-Kady; Nasser S M Ismail; Samy F Mahmoud; Hanem M Awad; Wael A El-Sayed
Journal:  Molecules       Date:  2021-06-26       Impact factor: 4.411
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