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

被引：5

作者：

Li Yanjie ^{[1
,2
]}

Zhang Xingmin ^{[3
]}

Niu Shengxiu ^{[1
]}

Zhao Yanping ^{[1
]}

Yang Lijuan ^{[1
]}

Shao Xiaowei ^{[1
]}

Wang Ensi ^{[1
]}

机构：

[1] Jilin Univ, Coll Pharm, Changchun 130021, Jilin, Peoples R China

[2] Changchun Univ Tradit Chinese Med, Coll Pharm, Changchun 130117, Jilin, Peoples R China

[3] Beijing Foreland Pharma Biol Technol Co Ltd, Beijing 101111, Peoples R China

来源：

CHEMICAL RESEARCH IN CHINESE UNIVERSITIES | 2017年 / 33卷 / 06期

关键词：

Imninzo[4,5-c]quinoline; Suzuki reaction; Dual PI3K/mTOR inhibitor; NVP-BEZ235; TARGET; MUTATIONS; RAPAMYCIN; GROWTH; CANCER;

D O I：

10.1007/s40242-017-7074-1

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A series of imidazo[4,5-c]quinoline derivatives(12a-12m) was synthesized with 2-amino-5-bromobenzoic 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 H-1-INMR, C-13 NMR and HRMS. These compounds show an interesting kinase profile as dual PI3K/mTOR tool compounds.

引用

页码：895 / 902

页数：8

共 50 条

[41] Design, Synthesis, and Biological Evaluation of Dimorpholine Substituted Thienopyrimidines as Potential Class I PI3K/mTOR Dual Inhibitors
Zhan, Miao
Deng, Yufang
Zhao, Lifeng
Yan, Guoyi
Wang, Fangying
Tian, Ye
Zhang, Lanxi
Jiang, Hongxia
Chen, Yuanwei
JOURNAL OF MEDICINAL CHEMISTRY, 2017, 60 (09) : 4023 - 4035
[42] Discovery of [1,2,3]Triazolo[4,5-c]quinoline Derivatives as a New Class of Ataxia-Telangiectasia Mutated Kinase Inhibitors
Zhang, Shiyu
Zhou, Pei
Liu, Jingming
Xia, Anjie
Lin, Guifeng
Xiang, Zhiyu
Fang, Zhen
Yang, Xin
Qiao, Jingxin
Hu, Qian
Zhang, Jiahao
Zhao, Jinlong
Li, Linli
ACS MEDICINAL CHEMISTRY LETTERS, 2023, 14 (06): : 746 - 756
[43] Design, Synthesis and Molecular Docking Studies of Pyrazoline Derivatives as PI3K Inhibitors
Kumar, Rohit
Kumar, Arvind
Kumar, Adarsh
Singh, Ankit Kumar
Kumar, Pradeep
COMBINATORIAL CHEMISTRY & HIGH THROUGHPUT SCREENING, 2024, 27 (02) : 256 - 272
[44] Design, synthesis and biological evaluation of novel chromeno[4,3-c] pyrazol-4(2H)-one derivates containing sulfonamido as potential PI3Kα inhibitors
Yin, Yong
Hu, Jia-Qin
Wu, Xu
Sha, Shao
Wang, She-Feng
Qiao, Fang
Song, Zhong-Cheng
Zhu, Hai-Liang
BIOORGANIC & MEDICINAL CHEMISTRY, 2019, 27 (11) : 2261 - 2267
[45] Design and synthesis of a novel pyrrolidinyl pyrido pyrimidinone derivative as a potent inhibitor of PI3Kα and mTOR
Le, Phuong T.
Cheng, Hengmiao
Ninkovic, Sacha
Plewe, Michael
Huang, Xiaojun
Wang, Hai
Bagrodia, Shubha
Sun, Shaoxian
Knighton, Daniel R.
Rogers, Caroline M. LaFleur
Pannifer, Andrew
Greasley, Samantha
Dalvie, Deepak
Zhang, Eric
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2012, 22 (15) : 5098 - 5103
[46] Recent Developments of Small Molecule PI3K/mTOR Dual Inhibitors
Liu, Yan-Na
Wan, Ren-Zhong
Liu, Zhao-Peng
MINI-REVIEWS IN MEDICINAL CHEMISTRY, 2013, 13 (14) : 2047 - 2059
[47] Design, Synthesis, and Biological Evaluation of Substituted Pyrimidines as Potential Phosphatidylinositol 3-Kinase (PI3K) Inhibitors
Zhang, Ji-Quan
Luo, Yong-Jie
Xiong, Yan-Shi
Yu, Yang
Tu, Zheng-Chao
Long, Zi-Jie
Lai, Xiao-Ju
Chen, Hui-Xuan
Luo, Yu
Weng, Jiang
Lu, Gui
JOURNAL OF MEDICINAL CHEMISTRY, 2016, 59 (15) : 7268 - 7274
[48] A Practical, Protecting-Group-Free Synthesis of a PI3K/mTOR Inhibitor
Tian, Qingping
Hoffmann, Ursula
Humphries, Theresa
Cheng, Zhigang
Hidber, Pirmin
Yajima, Herbert
Guillemot-Plass, Maud
Li, Jane
Bromberger, Ulrike
Babu, Srinivasan
Askin, David
Gosselin, Francis
ORGANIC PROCESS RESEARCH & DEVELOPMENT, 2015, 19 (03) : 416 - 426
[49] 3D-QSAR, Virtual Screening, Docking and Design of Dual PI3K/mTOR Inhibitors with Enhanced Antiproliferative Activity
Oluic, Jelena
Nikolic, Katarina
Vucicevic, Jelica
Gagic, Zarko
Filipic, Slavica
Agbaba, Danica
COMBINATORIAL CHEMISTRY & HIGH THROUGHPUT SCREENING, 2017, 20 (04) : 292 - 303
[50] Differential modulation of PI3K/Akt/mTOR activity by EGFR inhibitors: A rationale for co-targeting EGFR and PI3K in cisplatin-resistant HNSCC
Liao, Jipei
Yang, Zejia
Abarzarzin, Shirin
Cullen, Kevin J.
Dan, Hancai
HEAD AND NECK-JOURNAL FOR THE SCIENCES AND SPECIALTIES OF THE HEAD AND NECK, 2024, 46 (05): : 1126 - 1135

← 1 2 3 4 5 →