2016-2015
首页  科学研究  发表论文  2016-2015

Construction of Turmerone Motif-fused Spiropyrrolidine Oxindoles and Their Biological Evaluation for Anticancer Activities(Tetrahedron Letters 2016, 57, 1385–1389)

Graphic Abstract

 

  

ABSTRACT

Developed herein is a facile and efficient methodology toward the synthesis of novel turmerone motif-fused spiropyrrolidine oxindoles via a multicomponent 1,3-dipolar cycloaddition event of dienones 2 with azomethine ylides (thermally generated in situ from isatin derivatives and sarcosine).Products bearing adjacentquaternary-tertiary centers were smoothly obtained in high yields (up to 93% yield) with good diastereoselectivity (up to >20:1). In addition, their biological activity has been preliminarily demonstrated by in vitroevaluation againsthuman lung cancer cells A549 and human leukemia cellsK562 by the MTT-based assays, using the commercially available standard drug of Cisplatin as a positive control.The results also demonstrated that most of the compounds showed considerable cytotoxicities to these two cell lines of K562 andA549, showed comparably potent or even more potent than the positive control of Cisplatin (up to 5.1 times), and indicated that novel turmerone motif-fused spiropyrrolidine oxindoles may be potential leads for further biological screenings and may generate drug-like molecules.