N-<2-<<2-hydroxy-3-(3,4-dihydroxyphenoxy)propyl>amino>ethyl>-2-methylpropanamide | 53672-71-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: N-<2-<<2-hydroxy-3-(3,4-dihydroxyphenoxy)propyl>amino>ethyl>-2-methylpropanamide
• 英文别名: 1-(3,4-dihydroxyphenoxy)-3-β-isobutyramidoethyl-amino-2-propanol；1-(3,4-dihydroxyphenoxy)-3-β-isobutyramidoethylamino-2-propanol；N-[2-[[3-(3,4-dihydroxyphenoxy)-2-hydroxypropyl]amino]ethyl]-2-methylpropanamide
• CAS: 53672-71-2
• 化学式: C₁₅H₂₄N₂O₅
• 分子量: 312.366
• InChiKey: ISUNQCFDIPDPCF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  22
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  111
• 氢给体数：
  5
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  N-<2-(benzylamino)ethyl>isobutyramide 在 palladium on activated charcoal 氢气 、 溶剂黄146 作用下， 以 异丙醇 为溶剂， 反应 4.5h， 生成 N-<2-<<2-hydroxy-3-(3,4-dihydroxyphenoxy)propyl>amino>ethyl>-2-methylpropanamide
  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

• CH605666
  申请人：——

  公开号：——

  公开（公告）日：——
• US4131685A
  申请人：——

  公开号：US4131685A

  公开（公告）日：1978-12-26
• US4167581A
  申请人：——

  公开号：US4167581A

  公开（公告）日：1979-09-11
• .beta.-Adrenoceptor stimulant properties of amidoalkylamino-substituted 1-aryl-2-ethanols and 1-(aryloxy)-2-propanols
  作者：Jeffrey J. Barlow、Brian G. Main、H. Michael Snow

  DOI：10.1021/jm00135a015

  日期：1981.3

  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.