Diversity-oriented one-pot multicomponent synthesis of spirooxindole derivatives and their biological evaluation for anticancer activities. Issue 52 (29th December 2016)

• Record Type: Journal Article
• Authors: Yang, Jun; Liu, Xiong-Wei; Wang, Dan-Dan; Tian, Min-Yi; Han, Shuo-Nan; Feng, Ting-Ting; Liu, Xiong-Li; Mei, Ren-Qiang; Zhou, Ying
• Is Part Of: Tetrahedron. Volume 72:Issue 52(2016)
• Page Start: 8523
• Page End: 8536
• Publication Date: 2016-12-29
• Subjects: Five-membered carbocyclic spirooxindoles -- One-pot multicomponent synthesis -- Knoevenagel condensation/Michael/cyclization -- Aminomethylation -- Antitumor activity; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tet.2016.10.050
• Languages: English
• ISSNs: 0040-4020

Abstract

Abstract: Described herein is a facile and efficient methodology for diversity-oriented one-pot multicomponent synthesis of 3-aminomethyl quaternary carbon oxindole fused five-membered carbocyclic spirooxindoles5 via knoevenagel condensation/Michael/cyclization and then aminomethylation reaction. A wide variety of products with varying degrees of substitution around it, were obtained smoothly with high efficiency (up to overall yield 73% and >20:1 diastereoselectivity). In particular, their biological activities against these three cell lines K562, A549 and PC-3 have been evaluated. These results suggested that most of 3-aminomethyl quaternary carbon oxindole fused five-membered carbocyclic spirooxindoles5 showed equipotent or more potent than the positive control of Cisplatin (up to 3.4 times). Graphical abstract: Highlights: A methodology for synthesis of spirooxindole derivatives was developed. Products were obtained smoothly with high efficiency. Promising activities against three human cancer cell lines have been demonstrated.