Journal
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY
Volume 47, Issue -, Pages 312-322Publisher
ELSEVIER FRANCE-EDITIONS SCIENTIFIQUES MEDICALES ELSEVIER
DOI: 10.1016/j.ejmech.2011.10.058
Keywords
1H-pyrrole-2,5-diones; Azomethine ylides; Spiro[3H-indole-3,2 '(1 ' H)-pyrrolo[3,4-c]pyrrole]; Anti-tumor; QSAR
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Funding
- Swedish International Development Cooperation Agency (SIDA)
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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 4I exhibited high anti-tumor activity against HEPG2 (liver cancer) cell line (IC50 = 12.16 mu M) compared to that of Doxorubicin (IC50= 7.36 mu M), 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. (C) 2011 Elsevier Masson SAS. All rights reserved.
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