Core Scaffold-Inspired Concise Synthesis of Chiral Spirooxindole-Pyranopyrimidines with Broad-Spectrum Anticancer Potency

被引:107
作者
Jiang, Xianxing [1 ]
Sun, Yulong [1 ]
Yao, Jia [1 ]
Cao, Yiming [1 ]
Kai, Ming [1 ]
He, Ning [1 ]
Zhang, Xiaoyuan [1 ]
Wang, Yiqing [1 ]
Wang, Rui [1 ]
机构
[1] Lanzhou Univ, Key Lab Preclin Study New Drugs Gansu Prov, Inst Biochem & Mol Biol, Cent Lab,Hosp 1, Lanzhou 730000, Peoples R China
基金
中国国家自然科学基金;
关键词
anticancer activity; asymmetric synthesis; pyranopyrimidines; spiroheterocycles; DOUBLY STEREOCONTROLLED APPROACH; ENANTIOSELECTIVE SYNTHESIS; ASYMMETRIC CATALYSIS; MANNICH REACTION; OXINDOLES; CONSTRUCTION; DISCOVERY; EFFICIENT; THIOUREAS; AMINE;
D O I
10.1002/adsc.201100792
中图分类号
O69 [应用化学];
学科分类号
081704 ;
摘要
Due to the lack of tumor-specific anticancer agents, the discovery and development of new types of highly selective anticancer agents is still a very urgent topic. Herein, we present our contribution to concise construction of novel chiral spirooxindole-type pyranopyrimidines exhibiting a unique profile of biological activities. We have found that this new type of spiro alkaloid could inhibit the proliferation of various cancer cells in a preliminary biological evaluation. These findings suggested that spirooxindole-type pyranopyrimidines, developed by an asymmetric Michael/cyclization strategy, can potentially serve as a new kind of anticancer candidate.
引用
收藏
页码:917 / 925
页数:9
相关论文
共 53 条
[51]   Cascade Michael-Aldol reactions promoted by hydrogen bonding mediated catalysis [J].
Zu, Liansuo ;
Wang, Jian ;
Li, Hao ;
Xie, Hexin ;
Jiang, Wei ;
Wang, Wei .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (05) :1036-1037
[52]   Cooperative catalysis by tertiary amino-thioureas: Mechanism and basis for enantioselectivity of ketone cyanosilylation [J].
Zuend, Stephan J. ;
Jacobsen, Eric N. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (51) :15872-15883
[53]   Mechanism of Amido-Thiourea Catalyzed Enantioselective Imine Hydrocyanation: Transition State Stabilization via Multiple Non-Covalent Interactions [J].
Zuend, Stephan J. ;
Jacobsen, Eric N. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2009, 131 (42) :15358-15374