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Chinese Journal of Organic Chemistry >

2022 , Vol. 42 >Issue 1: 249 - 256

DOI: https://doi.org/10.6023/cjoc202107026

ARTICLES

Synthesis and Antitumor Activity of 2,4,6-Trisubstituted Novel Quinazoline Derivatives Containing Trifluoromethyl

  • Zhengjie Wang ,
  • Honglin Dai ,
  • Xiaojie Si ,
  • Chao Gao ,
  • Limin Liu ,
  • Luye Zhang ,
  • Yang Zhang ,
  • Yadan Song ,
  • Peirong Zhao ,
  • Jiaxin Zheng ,
  • Yu Ke ,
  • Hongmin Liu ,
  • Qiurong Zhang
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  • a School of Pharmaceutical Sciences, Zhengzhou University, Zhengzhou 450001
    b Collaborative Innovation Center of New Drug Research and Safety Evaluation, Zhengzhou University, Zhengzhou 450001
    c State Key Laboratory of Esophageal Cancer Prevention & Treatment, Zhengzhou University, Zhengzhou, 450052
    d Key Laboratory of Advanced Drug Preparation Technologies, Ministry of Education of China, Zhengzhou University, Zhengzhou 450001
* Corresponding authors. E-mail: ;
;

Received date: 2021-07-12

  Revised date: 2021-08-13

  Online published: 2021-08-29

Supported by

National Natural Science Foundation of China(U1904163); National Key Research Program of Proteins(2018YFE0195100); Opening Fund from State Key Laboratory of Esophageal Cancer Prevention & Treatment(K2020000X)

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Abstract

In order to find efficient and low toxicity antitumor drugs, a series of novel 2,4,6-trisubstituted quinazoline derivatives containing trifluoromethyl were synthesized and evaluated for their antitumor activities against human cancer cell lines (PC-3, MCF-7, Eca-109, MGC-803, HGC-27, A549, H1975) by using methyl thiazolyl tetrazolium (MTT) assay. Most of compounds exerted moderate to excellent antitumor activity against seven human cancer cells. Among them, N-(3-bromophenyl)-6-methoxy-2-((4-(trifluoromethyl)benzyl)thio)quinazolin-4-amine (16l) showed the best antitumor activity against PC-3 cancer cell line, with the IC50 values of (2.22±0.15) μmol/L, which was better than the positive control of gefitinib. At the same time, and compound 16l could dose-dependently and time-dependently induce PC-3 cells apoptosis.

Key words： trifluoromethyl; quinazoline; synthesis; antitumor activity

Cite this article

Zhengjie Wang , Honglin Dai , Xiaojie Si , Chao Gao , Limin Liu , Luye Zhang , Yang Zhang , Yadan Song , Peirong Zhao , Jiaxin Zheng , Yu Ke , Hongmin Liu , Qiurong Zhang . Synthesis and Antitumor Activity of 2,4,6-Trisubstituted Novel Quinazoline Derivatives Containing Trifluoromethyl[J]. Chinese Journal of Organic Chemistry, 2022 , 42(1) : 249 -256 . DOI: 10.6023/cjoc202107026

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