5-<1-hydroxy-2-ethyl>-1-methyl-1H-indole-7-carboxamide | 101544-46-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 5-<1-hydroxy-2-ethyl>-1-methyl-1H-indole-7-carboxamide
• 英文别名: 5-[1-hydroxy-2-(bis(phenylmethyl)amino)ethyl]-1-methyl-1H-indole-7-carboxamide；5-[2-(dibenzylamino)-1-hydroxyethyl]-1-methylindole-7-carboxamide
• CAS: 101544-46-1
• 化学式: C₂₆H₂₇N₃O₂
• 分子量: 413.519
• InChiKey: RPNXVMLCWOOXHS-UHFFFAOYSA-N

物化性质

• 熔点：
  163-165 °C
• 沸点：
  636.5±55.0 °C(Predicted)
• 密度：
  1.18±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.01
• 重原子数：
  31.0
• 可旋转键数：
  8.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  71.49
• 氢给体数：
  2.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  苄基丙酮 、 5-<1-hydroxy-2-ethyl>-1-methyl-1H-indole-7-carboxamide 在 platinum(IV) oxide 、 palladium on activated charcoal 氢气 、 溶剂黄146 作用下， 以 甲醇 为溶剂， 以800 mg的产率得到5-<1-hydroxy-2-<(1-methyl-3-phenylpropyl)-amino>ethyl>-1-methyl-1H-indole-7-carboxamide
  参考文献：
  名称：

  Indole-phenol-bioisosterism. Synthesis and antihypertensive activity of a pyrrolo analog of labetalol

  摘要：

  The synthesis of 5-[hydroxy-2-[(1-methyl-3-phenylpropyl)amino]ethyl]-1H-indole-7- carboxamide, 5, a pyrrolo analogue of labetalol, is described. Compound 5 was found to reduce blood pressure in spontaneously hypertensive rats with an ED50 of 5 mg/kg po, without causing any decrease in heart rate. Isolated tissue studies with 5 shows that it is a nonselective beta-adrenoceptor antagonist and that it is a weaker alpha-adrenoceptor antagonist with a relative selectivity for alpha 1-receptors. Additionally, the compound displayed significant beta-adrenoceptor intrinsic sympathomimetic activity. Evidence is presented that the beta-adrenoceptor antagonist and agonist properties of 5 are mediated via hydrogen-bond formation with the receptor.

  DOI：

  10.1021/jm00156a019
• 作为产物：
  描述：

  1-乙酰基-5-(氯乙酰基)二氢吲哚 在 吡啶 、 盐酸 、 potassium cyanide 、 manganese(IV) oxide 、 sodium hydroxide 、 sodium tetrahydroborate 、 tetrafluoroboric acid 、 双氧水 、 硝酸 、 sodium hydride 、 溶剂黄146 、 锌 、 sodium nitrite 作用下， 以 四氢呋喃 、 乙醇 、 溶剂黄146 、 二甲基亚砜 、 N,N-二甲基甲酰胺 为溶剂， 反应 29.58h， 生成 5-<1-hydroxy-2-ethyl>-1-methyl-1H-indole-7-carboxamide
  参考文献：
  名称：

  Indole-phenol-bioisosterism. Synthesis and antihypertensive activity of a pyrrolo analog of labetalol

  摘要：

  The synthesis of 5-[hydroxy-2-[(1-methyl-3-phenylpropyl)amino]ethyl]-1H-indole-7- carboxamide, 5, a pyrrolo analogue of labetalol, is described. Compound 5 was found to reduce blood pressure in spontaneously hypertensive rats with an ED50 of 5 mg/kg po, without causing any decrease in heart rate. Isolated tissue studies with 5 shows that it is a nonselective beta-adrenoceptor antagonist and that it is a weaker alpha-adrenoceptor antagonist with a relative selectivity for alpha 1-receptors. Additionally, the compound displayed significant beta-adrenoceptor intrinsic sympathomimetic activity. Evidence is presented that the beta-adrenoceptor antagonist and agonist properties of 5 are mediated via hydrogen-bond formation with the receptor.

  DOI：

  10.1021/jm00156a019

文献信息

• ASSELIN A. A.; HUMBER L. G.; CROSILLA D.; OSHIRO G.; WOJDAN A.; GRIMES D.+, J. MED. CHEM., 29,(1986) N 6, 1009-1015
  作者：ASSELIN A. A.、 HUMBER L. G.、 CROSILLA D.、 OSHIRO G.、 WOJDAN A.、 GRIMES D.+

  DOI：——

  日期：——