N-(4-(6,7-dimethoxy-4-morpholinoquinazolin-2-yl)phenyl)acetamide

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 英文名称: N-(4-(6,7-dimethoxy-4-morpholinoquinazolin-2-yl)phenyl)acetamide
• 英文别名: N-[4-(6,7-dimethoxy-4-morpholin-4-ylquinazolin-2-yl)phenyl]acetamide
• 化学式: C₂₂H₂₄N₄O₄
• 分子量: 408.457
• InChiKey: CLGRSHQUXJBWGX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  30
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  85.8
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  2,4-二氯-6,7-二甲氧基喹唑啉 在 (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride 、 sodium carbonate 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 乙二醇二甲醚 、 水 为溶剂， 反应 4.5h， 生成 N-(4-(6,7-dimethoxy-4-morpholinoquinazolin-2-yl)phenyl)acetamide
  参考文献：
  名称：

  Synthesis and antitumor activities evaluation of m-(4-morpholinoquinazolin-2-yl)benzamides in vitro and in vivo

  摘要：

  In the present study, a series of m-(4-morpholinoquinazolin-2-yl)benzamides were designed, synthesized and characterized. The antiproliferative activities of the synthesized compounds were evaluated against two human cell lines (HCF-116 and MCF-7). Compounds with IC50 values below 4 mu M were further evaluated against U-87 MG and A549 cell lines. Among these evaluated compounds, compound T10 displayed a remarkable antiproliferative effect in vitro. The hoechst staining assay showed that compound T10 caused morphological changes. The cell cycle and apoptosis assay further indicated that compound T10 can arrest HCT-116 cells in G2/M and G0/G1 phase and induce apoptosis. PI3K enzyme assays indicated that compounds 17 and T10 selectively inhibit PI3K alpha. A Western bolt assay further suggested that compound T10 can block the PI3K/Akt/mTOR pathway. Moreover, compound T10 inhibited tumor growth on a mice S180 homograft model. These findings directly identify m-(4-morpholinoquinazolin-2-yl)benzamide derivatives as novel anticancer agents. (C) 2015 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2015.04.037

文献信息

• AMIDO COMPOUNDS AS AhR MODULATORS
  申请人：IDEAYA BIOSCIENCES, INC.

  公开号：US20210115016A1

  公开（公告）日：2021-04-22

  Provided herein are compounds, compositions and methods of using the compounds and compositions for the treatment of diseases modulated, as least in part, by AhR. The compounds are represented by formulae Formula (I), (II), (III), (iv): wherein the letters and symbols a, b, c, d, e, f, g, Z, R 1b , R 2a and R 2b have the meanings provided in the specification.
• Synthesis and antitumor activities evaluation of m-(4-morpholinoquinazolin-2-yl)benzamides in vitro and in vivo
  作者：Xiao-Meng Wang、Min-Hang Xin、Jing Xu、Bo-Rui Kang、Yan Li、She-Min Lu、San-Qi Zhang

  DOI：10.1016/j.ejmech.2015.04.037

  日期：2015.5

  In the present study, a series of m-(4-morpholinoquinazolin-2-yl)benzamides were designed, synthesized and characterized. The antiproliferative activities of the synthesized compounds were evaluated against two human cell lines (HCF-116 and MCF-7). Compounds with IC50 values below 4 mu M were further evaluated against U-87 MG and A549 cell lines. Among these evaluated compounds, compound T10 displayed a remarkable antiproliferative effect in vitro. The hoechst staining assay showed that compound T10 caused morphological changes. The cell cycle and apoptosis assay further indicated that compound T10 can arrest HCT-116 cells in G2/M and G0/G1 phase and induce apoptosis. PI3K enzyme assays indicated that compounds 17 and T10 selectively inhibit PI3K alpha. A Western bolt assay further suggested that compound T10 can block the PI3K/Akt/mTOR pathway. Moreover, compound T10 inhibited tumor growth on a mice S180 homograft model. These findings directly identify m-(4-morpholinoquinazolin-2-yl)benzamide derivatives as novel anticancer agents. (C) 2015 Elsevier Masson SAS. All rights reserved.