2-(3-amino-4-(2-methoxyethoxy)phenyl)-5-phenylbenzoxazole | 599202-73-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 2-(3-amino-4-(2-methoxyethoxy)phenyl)-5-phenylbenzoxazole
• 英文别名: 2-(2-Methoxyethoxy)-5-(5-phenyl-1,3-benzoxazol-2-yl)aniline
• CAS: 599202-73-0
• 化学式: C₂₂H₂₀N₂O₃
• 分子量: 360.412
• InChiKey: SSJIALOCJRGELY-UHFFFAOYSA-N

物化性质

• 沸点：
  549.5±50.0 °C(Predicted)
• 密度：
  1.218±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  27
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  70.5
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  偏苯三酸酐 、 2-(3-amino-4-(2-methoxyethoxy)phenyl)-5-phenylbenzoxazole 在 溶剂黄146 作用下， 生成 2-[2-(2-methoxyethoxy)-5-(5-phenylbenzoxazol-2-yl)phenyl]-1,3-dioxo-2,3-dihydro-1H-isoindole-5-carboxylic acid
  参考文献：
  名称：

  2,3-Dihydro-1,3-dioxo-1H-isoindole-5-carboxylic acid derivatives: a novel class of small molecule heparanase inhibitors

  摘要：

  A novel class of 2,3-dihydro-1,3-dioxo-1H-isoindole-5-carboxylic acids are described as inhibitors of the endo-beta-glucuronidase heparanase. Several of the compounds, for example, 2-[4-propylamino-5-[5-(4-chloro)phenyl-benzoxazol-2-yl]phenyl]-2,3-dihydro-1,3-dioxo-IH-isoindole-5-carboxylic acid (9c), display potent heparanase inhibitory activity (IC50 200-500nM) and have high selectivity ( > 100-fold) over human beta-glucuronidase. They also show anti-angiogenic effects. Such compounds should serve as useful biological tools and may provide a basis for the design of novel therapeutic agents. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.03.086
• 作为产物：
  描述：

  苯硼酸 在 palladium on activated charcoal 四(三苯基膦)钯 、 氢气 、 sodium carbonate 作用下， 以 1,4-二氧六环 、 乙酸乙酯 为溶剂， 生成 2-(3-amino-4-(2-methoxyethoxy)phenyl)-5-phenylbenzoxazole
  参考文献：
  名称：

  2,3-Dihydro-1,3-dioxo-1H-isoindole-5-carboxylic acid derivatives: a novel class of small molecule heparanase inhibitors

  摘要：

  A novel class of 2,3-dihydro-1,3-dioxo-1H-isoindole-5-carboxylic acids are described as inhibitors of the endo-beta-glucuronidase heparanase. Several of the compounds, for example, 2-[4-propylamino-5-[5-(4-chloro)phenyl-benzoxazol-2-yl]phenyl]-2,3-dihydro-1,3-dioxo-IH-isoindole-5-carboxylic acid (9c), display potent heparanase inhibitory activity (IC50 200-500nM) and have high selectivity ( > 100-fold) over human beta-glucuronidase. They also show anti-angiogenic effects. Such compounds should serve as useful biological tools and may provide a basis for the design of novel therapeutic agents. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.03.086