4-(3'-chloroanilino)-7-methoxy-6-(prop-2-ynyloxy)quinazoline | 1214731-76-6

• 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: 4-(3'-chloroanilino)-7-methoxy-6-(prop-2-ynyloxy)quinazoline
• 英文别名: 4-(3''-Chloroanilino)-7-methoxy-6-(prop-2-ynyloxy)quinazoline；N-(3-chlorophenyl)-7-methoxy-6-prop-2-ynoxyquinazolin-4-amine
• CAS: 1214731-76-6
• 化学式: C₁₈H₁₄ClN₃O₂
• 分子量: 339.781
• InChiKey: WBACAQZZINXVMK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  56.3
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  聚合甲醛 、 4-(3'-chloroanilino)-7-methoxy-6-(prop-2-ynyloxy)quinazoline 在 二异丙胺 、 copper(I) bromide 作用下， 以 1,4-二氧六环 为溶剂， 反应 4.0h， 以50%的产率得到6-(buta-2,3-dienyloxy)-4-(3'-chlorophenylamino)-7-methoxyquinazoline
  参考文献：
  名称：

  Enhancement of EGFR tyrosine kinase inhibition by C–C multiple bonds-containing anilinoquinazolines

  摘要：

  A series of 4-anilinoquinazolines with C-C multiple bond substitutions at the 6-position were synthesized and investigated for their potential to inhibit epidermal growth factor receptor (EGFR) tyrosine kinase activity. Among the compounds synthesized, alkyne 6d and allenes 7d and 7f significantly inhibited EGFR tyrosine kinase activity. These compounds inhibited EGF-mediated phosphorylation of EGFR in A431 cells, resulting in cell-cycle arrest and apoptosis induction. The C-C multiple bonds substituted at the C-6 position of the anilinoquinazoline framework were essential for the significant inhibitory activity. Compounds with long carbon chains (n = 3-6), such as 6c-f, 7c-f, 11, and 12, displayed prolonged inhibitory activity. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2009.11.035
• 作为产物：
  描述：

  4-(3-氯苯胺基)-7-甲氧基喹唑啉-6-醇 、 3-溴丙炔 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 12.0h， 以88%的产率得到4-(3'-chloroanilino)-7-methoxy-6-(prop-2-ynyloxy)quinazoline
  参考文献：
  名称：

  Enhancement of EGFR tyrosine kinase inhibition by C–C multiple bonds-containing anilinoquinazolines

  摘要：

  A series of 4-anilinoquinazolines with C-C multiple bond substitutions at the 6-position were synthesized and investigated for their potential to inhibit epidermal growth factor receptor (EGFR) tyrosine kinase activity. Among the compounds synthesized, alkyne 6d and allenes 7d and 7f significantly inhibited EGFR tyrosine kinase activity. These compounds inhibited EGF-mediated phosphorylation of EGFR in A431 cells, resulting in cell-cycle arrest and apoptosis induction. The C-C multiple bonds substituted at the C-6 position of the anilinoquinazoline framework were essential for the significant inhibitory activity. Compounds with long carbon chains (n = 3-6), such as 6c-f, 7c-f, 11, and 12, displayed prolonged inhibitory activity. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2009.11.035

文献信息

• Enhancement of EGFR tyrosine kinase inhibition by C–C multiple bonds-containing anilinoquinazolines
  作者：Hyun Seung Ban、Yuko Tanaka、Wataru Nabeyama、Masako Hatori、Hiroyuki Nakamura

  DOI：10.1016/j.bmc.2009.11.035

  日期：2010.1

  A series of 4-anilinoquinazolines with C-C multiple bond substitutions at the 6-position were synthesized and investigated for their potential to inhibit epidermal growth factor receptor (EGFR) tyrosine kinase activity. Among the compounds synthesized, alkyne 6d and allenes 7d and 7f significantly inhibited EGFR tyrosine kinase activity. These compounds inhibited EGF-mediated phosphorylation of EGFR in A431 cells, resulting in cell-cycle arrest and apoptosis induction. The C-C multiple bonds substituted at the C-6 position of the anilinoquinazoline framework were essential for the significant inhibitory activity. Compounds with long carbon chains (n = 3-6), such as 6c-f, 7c-f, 11, and 12, displayed prolonged inhibitory activity. (C) 2009 Elsevier Ltd. All rights reserved.