6,7-二甲氧基-4-(3-乙酰氧基苯氧基)喹啉 | 651054-54-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 6,7-二甲氧基-4-(3-乙酰氧基苯氧基)喹啉
• 英文名称: 6,7-dimethoxy-4-(3-acetoxyphenoxy)quinoline
• CAS: 651054-54-5
• 化学式: C₁₉H₁₇NO₅
• 分子量: 339.348
• InChiKey: QFPNVJWZFTWUKX-UHFFFAOYSA-N

物化性质

• 沸点：
  488.6±45.0 °C(Predicted)
• 密度：
  1.243±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.97
• 重原子数：
  25.0
• 可旋转键数：
  5.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  66.88
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  6,7-二甲氧基-4-(3-乙酰氧基苯氧基)喹啉 在 potassium carbonate 作用下， 以 甲醇 、 氯仿 为溶剂， 以92%的产率得到6,7-dimethoxy-4-(3-hydroxyphenoxy)quinoline
  参考文献：
  名称：

  Synthesis and structure–activity relationship for new series of 4-Phenoxyquinoline derivatives as specific inhibitors of platelet-derived growth factor receptor tyrosine kinase

  摘要：

  We discovered a new series of 4-phenoxyquinoline derivatives as potent and selective inhibitors of the platelet-derived growth factor receptor (PDGFr) tyrosine kinase. We researched the highly potent and selective inhibitors on the basis of both PDGFr and epidermal growth factor receptor (EGFr) inhibitory activity. First, we found a compound, Ki6783 (1), which inhibited PDGFr autophosphorylation at 0.13 muM, but it did not inhibit EGFr autophosphorylation at 100 muM. After extensive explorations, we found the two desired compounds, Ki6896 (2) and Ki6945 (3), which are substituted by benzoyl and benzamide at the 4-position of the phenoxy group on 4-phenoxyquinoline, respectively. These inhibitory activities were 0.31 and 0.050 muM, respectively, but neither of them inhibited EGFr autophosphorylation at 100 M. We further investigated the profile of both compounds toward various tyrosine and serine/threonine kinases. The three compounds specifically inhibited PDGFr rather than the other kinases. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2003.08.020
• 作为产物：
  描述：

  ethyl 4-hydroxy-6,7-dimethoxyquinoline-3-carboxylate 在 sodium hydroxide 、 三氯氧磷 作用下， 以 甲醇 、 二苯醚 为溶剂， 反应 2.83h， 生成 6,7-二甲氧基-4-(3-乙酰氧基苯氧基)喹啉
  参考文献：
  名称：

  Synthesis and structure–activity relationship for new series of 4-Phenoxyquinoline derivatives as specific inhibitors of platelet-derived growth factor receptor tyrosine kinase

  摘要：

  We discovered a new series of 4-phenoxyquinoline derivatives as potent and selective inhibitors of the platelet-derived growth factor receptor (PDGFr) tyrosine kinase. We researched the highly potent and selective inhibitors on the basis of both PDGFr and epidermal growth factor receptor (EGFr) inhibitory activity. First, we found a compound, Ki6783 (1), which inhibited PDGFr autophosphorylation at 0.13 muM, but it did not inhibit EGFr autophosphorylation at 100 muM. After extensive explorations, we found the two desired compounds, Ki6896 (2) and Ki6945 (3), which are substituted by benzoyl and benzamide at the 4-position of the phenoxy group on 4-phenoxyquinoline, respectively. These inhibitory activities were 0.31 and 0.050 muM, respectively, but neither of them inhibited EGFr autophosphorylation at 100 M. We further investigated the profile of both compounds toward various tyrosine and serine/threonine kinases. The three compounds specifically inhibited PDGFr rather than the other kinases. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2003.08.020