期刊
TETRAHEDRON
卷 74, 期 9, 页码 932-947出版社
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2017.12.049
关键词
Tetrahydroquinolines; Multicomponent reaction; Mannich-type reaction; Anticancer activity; Cell cycle arrest
资金
- COLCIENCIAS
- Universidad del Valle [CI-7812]
- Chemistry Department of the Universidad de los Andes
- Faculty of Science of the Universidad de los Andes
A useful and efficient method to construct diversely substituted 1,2,3,4-tetrahydroquinolines in good to excellent yields has been developed through a catalyst-free Domino Mannich and intramolecular Friedel-Crafts alkylation reactions of N-arylamines with paraformaldehyde and electron-rich olefins via the formation of N-aryl-N-alkylmethyleneiminium ions as the key intermediates to afford the target products. Nine of the new compounds were evaluated in the US National Cancer Institute (NCI), where compound 5f (R1 = 6-MeO, R2 = p-ClC6H4 and X = pyrrolidin-2-onyl) presented a remarkable activity against 57 cancer cell lines, with the most important GI50 values ranging from 1.46 to 8.28 M from in vitro assays. Further studies performed over the active compound 5f on HCT116 colon cancer cells indicated that its effect on cell death is exerted through a cell cycle arrest (S phase) in a dose dependent manner, as well as suppression on the cell proliferation process. (C) 2018 Elsevier Ltd. All rights reserved.
作者
我是这篇论文的作者
点击您的名字以认领此论文并将其添加到您的个人资料中。
推荐
暂无数据