Issue 46, 2014

Highly regioselective synthesis of 3-alkenyl-oxindole ring-fused 3,3′-disubstituted oxindoles via direct gamma-substitution of Morita–Baylis–Hillman carbonates of isatins with 3-substituted oxindoles

Abstract

The first phase transfer-catalysed direct γ-substitution of Morita–Baylis–Hillman carbonates of isatins with 3-substituted oxindoles has been developed, which affords 3-alkenyl-oxindole ring-fused 3,3′-disubstituted oxindoles in up to 83% yield under mild reaction conditions. Furthermore, their biological activity has been preliminarily demonstrated by in vitro evaluation against human prostate cancer cells PC-3 and human leukemia cells K562, using MTT-based assays with the commercially available standard drug Cisplatin as a positive control. Gratifyingly, compounds 3aa, 3ba and 3ca exhibited comparable in vitro inhibitory activities against human prostate cancer cells (PC-3) to Cisplatin. What's more, 3ba also had a good inhibition ability against human leukemia cells K562. These results indicate that 3-alkenyl-oxindole ring-fused 3,3′-disubstituted oxindole analogs may be potential lead compounds for further biological screening.

Graphical abstract: Highly regioselective synthesis of 3-alkenyl-oxindole ring-fused 3,3′-disubstituted oxindoles via direct gamma-substitution of Morita–Baylis–Hillman carbonates of isatins with 3-substituted oxindoles

Supplementary files

Article information

Article type
Paper
Submitted
21 Jul 2014
Accepted
02 Oct 2014
First published
02 Oct 2014

Org. Biomol. Chem., 2014,12, 9366-9374

Highly regioselective synthesis of 3-alkenyl-oxindole ring-fused 3,3′-disubstituted oxindoles via direct gamma-substitution of Morita–Baylis–Hillman carbonates of isatins with 3-substituted oxindoles

T. Feng, X. Huang, X. Liu, D. Jing, X. Liu, F. Guo, Y. Zhou and W. Yuan, Org. Biomol. Chem., 2014, 12, 9366 DOI: 10.1039/C4OB01523A

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