phenyl N-<2--2-hydroxypropyl>amino>ethyl>carbamate | 69630-06-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: phenyl N-<2--2-hydroxypropyl>amino>ethyl>carbamate
• 英文别名: phenyl N-[2-(N-benzyl{3-[4-(benzyloxy)phenoxy]-2-hydroxypropyl}amino)ethyl]carbamate；phenyl N-[2-[benzyl-[2-hydroxy-3-(4-phenylmethoxyphenoxy)propyl]amino]ethyl]carbamate
• CAS: 69630-06-4
• 化学式: C₃₂H₃₄N₂O₅
• 分子量: 526.632
• InChiKey: GEUSHJQCJSEWHJ-UHFFFAOYSA-N

物化性质

• 沸点：
  687.5±55.0 °C(Predicted)
• 密度：
  1.204±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  39.0
• 可旋转键数：
  14.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  80.26
• 氢给体数：
  2.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  phenyl N-<2--2-hydroxypropyl>amino>ethyl>carbamate 在 palladium on activated charcoal 氢气 、 溶剂黄146 作用下， 以 甲苯 为溶剂， 反应 19.5h， 生成 扎莫特罗
  参考文献：
  名称：

  .beta.-Adrenoceptor stimulant properties of amidoalkylamino-substituted 1-aryl-2-ethanols and 1-(aryloxy)-2-propanols

  摘要：

  Parallel series of 2-[(2-amidoethyl)amino]-1-arylethanols and 1-[(2-amidoethyl)amino]-3-(aryloxy)-2-propanols have been prepared, and the compounds were tested as beta-adrenoceptor stimulants on the heart and circulation of the dog. The corresponding 2-(alkylamino)-1-arylethanols and 3-(alkylamino)-2-propanols have been tested for comparison and the structure-activity relationships (SAR) examined. The arylethanols are potent full agonists, showing selectivity for the heart relative to blood vessels, while the (aryloxy)propanols are even more cardioselective and are partial agonists. Within a narrow series of 1-[(amidoethyl)amino]-3-(4-hydroxyphenoxy)-2-propanols, careful examination of the SAR of the amide group showed that great variation in cardioselectivity and degree of agonism may be produce. From this study ICI 118587, N-[20[[2-hydroxy-3-(4-hydroxyphenoxy)propyl]amino]ethyl]-4-morpholinecarboxamide, was selected for its high cardioselectivity and 50% agonist properties. This compound in under clinical evaluation as a cardiac stimulant.

  DOI：

  10.1021/jm00135a015
• 作为产物：
  描述：

  N-<-2-hydroxypropyl>amino>ethyl>-2-methylpropanamide 在 氢氧化钾 、 碳酸氢钠 作用下， 以 乙醇 、 甲苯 为溶剂， 反应 96.0h， 生成 phenyl N-<2--2-hydroxypropyl>amino>ethyl>carbamate
  参考文献：
  名称：

  .beta.-Adrenoceptor stimulant properties of amidoalkylamino-substituted 1-aryl-2-ethanols and 1-(aryloxy)-2-propanols

  摘要：

  Parallel series of 2-[(2-amidoethyl)amino]-1-arylethanols and 1-[(2-amidoethyl)amino]-3-(aryloxy)-2-propanols have been prepared, and the compounds were tested as beta-adrenoceptor stimulants on the heart and circulation of the dog. The corresponding 2-(alkylamino)-1-arylethanols and 3-(alkylamino)-2-propanols have been tested for comparison and the structure-activity relationships (SAR) examined. The arylethanols are potent full agonists, showing selectivity for the heart relative to blood vessels, while the (aryloxy)propanols are even more cardioselective and are partial agonists. Within a narrow series of 1-[(amidoethyl)amino]-3-(4-hydroxyphenoxy)-2-propanols, careful examination of the SAR of the amide group showed that great variation in cardioselectivity and degree of agonism may be produce. From this study ICI 118587, N-[20[[2-hydroxy-3-(4-hydroxyphenoxy)propyl]amino]ethyl]-4-morpholinecarboxamide, was selected for its high cardioselectivity and 50% agonist properties. This compound in under clinical evaluation as a cardiac stimulant.

  DOI：

  10.1021/jm00135a015

文献信息

• BARLOW J. J.; MAIN B. G.; SNOW H. M., J. MED. CHEM., 1981, 24, NO 3, 315-322
  作者：BARLOW J. J.、 MAIN B. G.、 SNOW H. M.

  DOI：——

  日期：——
• MAIN, B. G.;BARLOW, J. J.
  作者：MAIN, B. G.、BARLOW, J. J.

  DOI：——

  日期：——