Issue 27, 2013
From the journal:

RSC Advances

Diversity-oriented synthesis of spiro-oxindole-based 2,5-dihydropyrroles via three-component cycloadditions and evaluation on their cytotoxicity†

Wei Tan,‡a   Xiao-Tong Zhu,‡b   Shu Zhang,*c   Gui-Juan Xing,a   Ren-Yi Zhua  and  Feng Shi*a  

* Corresponding authors

a School of Chemistry and Chemical Engineering, Jiangsu Normal University, Xuzhou, China
E-mail: fshi@jsnu.edu.cn
Fax: +86(516) 83500065
Tel: +86(516) 83403165

b Department of Chemistry, School of Basic Education Sciences, Xuzhou Medical College, Xuzhou, China

c Clinical Research Center, the First Affiliated Hospital of Nanjing Medical University, Nanjing, China
E-mail: zszqs@sina.com

Abstract

The construction of a spiro-oxindole-based 2,5-dihydropyrrole scaffold with potential bioactivity has been established via an efficient three-component reaction of isatin, amino-ester and alkyne. This protocol represents the first 1,3-dipolar cycloaddition of electron-deficient alkynes with isatin-derived azomethine ylides, providing an easy access to spiro-oxindole-based 2,5-dihydropyrroles with structural diversity in high yields (up to 99%). In addition, the bioscreen of these new spiro-dihydropyrroles has led to the finding of sixteen compounds with promising cytotoxicity to MCF-7 cells.

Graphical abstract: Diversity-oriented synthesis of spiro-oxindole-based 2,5-dihydropyrroles via three-component cycloadditions and evaluation on their cytotoxicity

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Article information

DOI
https://doi.org/10.1039/C3RA40874D
Article type
Paper
Submitted
20 Feb 2013
Accepted
15 Apr 2013
First published
16 Apr 2013

RSC Adv., 2013,3, 10875-10886

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Diversity-oriented synthesis of spiro-oxindole-based 2,5-dihydropyrroles via three-component cycloadditions and evaluation on their cytotoxicity

W. Tan, X. Zhu, S. Zhang, G. Xing, R. Zhu and F. Shi, RSC Adv., 2013, 3, 10875 DOI: 10.1039/C3RA40874D

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