N-(4-hydroxyphenyl)-5,6-dimethoxyphthalimide | 862211-41-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 英文名称: N-(4-hydroxyphenyl)-5,6-dimethoxyphthalimide
• 英文别名: 2-(4-Hydroxyphenyl)-5,6-dimethoxyisoindole-1,3-dione
• CAS: 862211-41-4
• 化学式: C₁₆H₁₃NO₅
• 分子量: 299.283
• InChiKey: PHCDNFHIGYQWAV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  76.1
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N-(4-hydroxyphenyl)-5,6-dimethoxyphthalimide 在 potassium carbonate 、 溶剂黄146 、 锌 作用下， 生成 N-[4-(2,3-epoxypropoxy)phenyl]-5,6-dimethoxy-1-oxo-isoindoline
  参考文献：
  名称：

  Synthesis of 4-(1-oxo-isoindoline) and 4-(5,6-dimethoxy-1-oxo-isoindoline)-substituted phenoxypropanolamines and their β1-, β2-adrenergic receptor binding studies

  摘要：

  Phenoxypropanolamines with 1-oxo-isoindoline (12-16) and 5,6-dimethoxy-1-oxo-isoindoline groups (17-20) at the para position were synthesized. beta(1), beta(2)-Adrenergic receptor binding affinities for the synthesized compounds were tested and compared with propranolol and atenolol. It was found that the incorporation of para-amidic functionality within the 1-oxo-isoindoline ring and 5,6-dimethoxy-1-oxo-isoindoline ring system led to a high degree of cardio selectivity in the phenoxypropanolamines. Two of the compounds 12 and 20 possessed beta(1)-adrenergic receptor affinity comparable with that of atenolol and both showed a better cardioselectivity than atenotol. Both 12 and 20 are undergoing further pharmacological evaluation. (c) 2005 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.bioorg.2005.05.001
• 作为产物：
  描述：

  4,5-二甲氧基邻苯二甲酸酐 、 对氨基苯酚 在 吡啶 作用下， 反应 2.0h， 以57.04%的产率得到N-(4-hydroxyphenyl)-5,6-dimethoxyphthalimide
  参考文献：
  名称：

  Synthesis of 4-(1-oxo-isoindoline) and 4-(5,6-dimethoxy-1-oxo-isoindoline)-substituted phenoxypropanolamines and their β1-, β2-adrenergic receptor binding studies

  摘要：

  Phenoxypropanolamines with 1-oxo-isoindoline (12-16) and 5,6-dimethoxy-1-oxo-isoindoline groups (17-20) at the para position were synthesized. beta(1), beta(2)-Adrenergic receptor binding affinities for the synthesized compounds were tested and compared with propranolol and atenolol. It was found that the incorporation of para-amidic functionality within the 1-oxo-isoindoline ring and 5,6-dimethoxy-1-oxo-isoindoline ring system led to a high degree of cardio selectivity in the phenoxypropanolamines. Two of the compounds 12 and 20 possessed beta(1)-adrenergic receptor affinity comparable with that of atenolol and both showed a better cardioselectivity than atenotol. Both 12 and 20 are undergoing further pharmacological evaluation. (c) 2005 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.bioorg.2005.05.001

文献信息

• Jindal, Dharam Paul; Singh, Babita; Coumar, Mohane Selvaraj, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2005, vol. 44, # 7, p. 1441 - 1445
  作者：Jindal, Dharam Paul、Singh, Babita、Coumar, Mohane Selvaraj、Bruni, Giancarlo、Massarelli, Paola

  DOI：——

  日期：——
• Synthesis of 4-(1-oxo-isoindoline) and 4-(5,6-dimethoxy-1-oxo-isoindoline)-substituted phenoxypropanolamines and their β1-, β2-adrenergic receptor binding studies
  作者：Dharam P. Jindal、Babita Singh、Mohane S. Coumar、Giancarlo Bruni、Paola Massarelli

  DOI：10.1016/j.bioorg.2005.05.001

  日期：2005.8

  Phenoxypropanolamines with 1-oxo-isoindoline (12-16) and 5,6-dimethoxy-1-oxo-isoindoline groups (17-20) at the para position were synthesized. beta(1), beta(2)-Adrenergic receptor binding affinities for the synthesized compounds were tested and compared with propranolol and atenolol. It was found that the incorporation of para-amidic functionality within the 1-oxo-isoindoline ring and 5,6-dimethoxy-1-oxo-isoindoline ring system led to a high degree of cardio selectivity in the phenoxypropanolamines. Two of the compounds 12 and 20 possessed beta(1)-adrenergic receptor affinity comparable with that of atenolol and both showed a better cardioselectivity than atenotol. Both 12 and 20 are undergoing further pharmacological evaluation. (c) 2005 Elsevier Inc. All rights reserved.