2014-2013
首页  科学研究  发表论文  2014-2013

Highly Regioselective Syntheses 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(Org. Biomol. Chem., 2014, 12, 9366–9374)

Graphic Abstract  

  

  

ABTRACT

The phase transfer-catalysed the first 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 condition. Furthermore, their biological activity has been preliminarily demonstrated by in vitroevaluation againsthuman prostate cancer cells PC-3 and human leukemia cells K562 by the MTT-based assays, using the commercially available standard drugs Cisplatin as a positive control. Gratifyingly, compounds 3aa, 3ba and 3caexhibited comparable in vitro inhibitory activity againsthuman prostate cancer cells (PC-3) with the positive control Cisplatin. What’s more, 3ba also had good inhibition ability against human leukemia cells K562. These resultsindicated that3-alkenyl-oxindole ring-fused 3,3′-disubstituted oxindole analogs may be potential lead compounds for further biological screenings.