Diversity-Oriented Synthesis of Imidazo-Dipyridines with Anticancer Activity via the Groebke-Blackburn-Bienayme and TBAB-Mediated Cascade Reaction in One Pot

被引：22
|
作者：
Li, Yong [1 ]
Huang, Jiu-Hong [1 ]
Wang, Juan-Li [1 ]
Song, Gui-Ting [1 ]
Tang, Dian-Yong [1 ]
Yao, Fang [1 ]
Lin, Hui-kuan [3 ]
Yan, Wei [2 ]
Li, Hong-yu [2 ]
Xu, Zhi-Gang [1 ]
Chen, Zhong-Zhu [1 ]
机构：
[1] Chongqing Univ Arts & Sci, Int Acad Targeted Therapeut & Innovat, 319 Honghe Ave, Chongqing 402160, Peoples R China
[2] Univ Arkansas Med Sci, Coll Pharm, Dept Pharmaceut Sci, Little Rock, AR 72205 USA
[3] Wake Forest Sch Med, Dept Canc Biol, Winston Salem, NC 27157 USA
来源：
JOURNAL OF ORGANIC CHEMISTRY | 2019年 / 84卷 / 19期
关键词：
MULTICOMPONENT REACTIONS; CYCLIZATION; SCAFFOLDS; DRUG; HETEROCYCLES; DERIVATIVES;
D O I：
10.1021/acs.joc.9b01385
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A facile and metal-free one-pot protocol for the synthesis of fused imidazopyridine scaffolds has been developed. This novel protocol combines the Groebke-Blackburn-Bienayme reaction (GBBR) with a sequential TBAB-mediated cyclization cascade. Biological evaluation demonstrated that compound 6a inhibits human prostate cancer cell DU-145 proliferation with an IC50 of 1.6 mu M. The molecular mechanism study indicates that 6a significantly suppresses the oncogenic Erk kinase phosphorylation at 3 mu M.
引用
收藏
页码：12632 / 12638
页数：7
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