Synthesis and Biological Activity of Imidazo[4,5-c]quinoline Derivatives as PI3K/mTOR Inhibitors

doi:10.1007/s40242-017-7074-1

Chemical Research in Chinese Universities ›› 2017, Vol. 33 ›› Issue (6): 895-902.doi: 10.1007/s40242-017-7074-1

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Synthesis and Biological Activity of Imidazo[4,5-c]quinoline Derivatives as PI3K/mTOR Inhibitors

LI Yanjie^1,2, ZHANG Xingmin³, NIU Shengxiu¹, ZHAO Yanping¹, YANG Lijuan¹, SHAO Xiaowei¹, WANG Ensi¹

1. College of Pharmacy, Jilin University, Changchun 130021, P. R. China;
2. College of Pharmacy, Changchun University of Traditional Chinese Medicine, Changchun 130117, P. R. China;
3. Beijing Foreland Pharma Biological Technology Co., Ltd., Beijing 101111, P. R. China

Received:2017-03-01 Revised:2017-03-29 Online:2017-12-01 Published:2017-07-21
Contact: WANG Ensi,E-mail:wangss@jlu.edu.cn E-mail:wangss@jlu.edu.cn
Supported by:
Supported by the Fund of Jilin University(China) Hi-Tech(Group) Co., Ltd.

Abstract

Abstract: A series of imidazo[4,5-c]quinoline derivatives(12a-12m) was synthesized with 2-amino-5-bromoben-zoic acid and 4-nitrophenylacetonitrile as starting materials, 6-bromo-4-chloro-3-nitroquinoline as intermediate and Suzuki reaction and closure of the imidazolinone ring with triphosgene as key steps. The structures of the key intermediate and target compounds were confirmed by means of ¹H NMR, ¹³C NMR and HRMS. These compounds show an interesting kinase profile as dual PI3K/mTOR tool compounds.

Key words: Imidazo[4,5-c]quinoline, Suzuki reaction, Dual PI3K/mTOR inhibitor

LI Yanjie, ZHANG Xingmin, NIU Shengxiu, ZHAO Yanping, YANG Lijuan, SHAO Xiaowei, WANG Ensi. Synthesis and Biological Activity of Imidazo[4,5-c]quinoline Derivatives as PI3K/mTOR Inhibitors[J]. Chemical Research in Chinese Universities, 2017, 33(6): 895-902.

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Synthesis and Biological Activity of Imidazo[4,5-c]quinoline Derivatives as PI3K/mTOR Inhibitors

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