Change search
ReferencesLink to record
Permanent link

Direct link
Design, synthesis and QSAR studies of dispiroindole derivatives as new antiproliferative agents
Stockholm University, Faculty of Science, Department of Organic Chemistry.
2013 (English)In: European Journal of Medicinal Chemistry, ISSN 0223-5234, E-ISSN 1768-3254, Vol. 68, 339-351 p.Article in journal (Refereed) Published
Abstract [en]

A variety of 4'-ary1-3-(arylmethylidene)-1 ''-[(cyclic-amino)methylene]-1'-methyl-dispiro[cyclohexane-1,3'-pyrrolidine-2',3 ''-[3H]indole]-2,2 ''(1H)-diones 4a-u were prepared via reaction of 2E,6E-bis(arylidene)-1-cyclohexanones 1a-i with azomethine ylides, generated in situ via a decarboxylative condensation of isatins 2a-c and sarcosine (3). Single crystal X-ray study of 4a, revealed structural and stereochemical features of these derivatives. While most of the synthesized compounds exhibit mild antitumor properties when tested against various human tumor cell lines (HEPG2 liver, HELA cervical and PD prostate cancers), three of them, 4d and 4p (active against HEPG2), and compound 4g (active against HELA), demonstrated higher activities, that were close or even higher than that of the reference standard Doxorubicin. QSAR studies revealed good predictive and statistically significant 3 descriptor models (r(2) = 0.903-0.812, r(adjusted)(2) = 0.855-0.672, r(prediction)(2) = 0.773-0.605).

Place, publisher, year, edition, pages
2013. Vol. 68, 339-351 p.
Keyword [en]
2, 6-Bis(arylidene)-1-cydohexanone, Spiropyrrolidine-oxindole, Azomethine ylide, Antitumor, QSAR
National Category
Pharmacology and Toxicology
URN: urn:nbn:se:su:diva-98095DOI: 10.1016/j.ejmech.2013.07.035ISI: 000326902300036OAI: diva2:682308
Sida - Swedish International Development Cooperation Agency


Available from: 2013-12-27 Created: 2013-12-27 Last updated: 2013-12-27Bibliographically approved

Open Access in DiVA

No full text

Other links

Publisher's full text

Search in DiVA

By author/editor
Stawinski, Jacek
By organisation
Department of Organic Chemistry
In the same journal
European Journal of Medicinal Chemistry
Pharmacology and Toxicology

Search outside of DiVA

GoogleGoogle Scholar
The number of downloads is the sum of all downloads of full texts. It may include eg previous versions that are now no longer available

Altmetric score

Total: 23 hits
ReferencesLink to record
Permanent link

Direct link