1-acetyl-5-<1-(acetyloxy)-2-ethyl>-2,3-dihydro-1H-indole-7-carbonitrile | 101544-42-7

• 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: 1-acetyl-5-<1-(acetyloxy)-2-ethyl>-2,3-dihydro-1H-indole-7-carbonitrile
• 英文别名: 1-acetyl-5-[2-(dibenzylamino)-1-acetyloxyethyl]-7-cyanoindoline；1-acetyl-5-[1-(acetyloxy)-2-(bis(phenylmethyl)amino)ethyl]-2,3-dihydro-1H-indole-7-carbonitrile；[1-(1-Acetyl-7-cyano-2,3-dihydroindol-5-yl)-2-(dibenzylamino)ethyl] acetate
• CAS: 101544-42-7
• 化学式: C₂₉H₂₉N₃O₃
• 分子量: 467.568
• InChiKey: GXBQVRABZOMFFI-UHFFFAOYSA-N

物化性质

• 熔点：
  108-109 °C(Solv: ethanol (64-17-5))
• 沸点：
  672.0±55.0 °C(Predicted)
• 密度：
  1.24±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  35
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  73.6
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1-acetyl-5-<1-(acetyloxy)-2-ethyl>-2,3-dihydro-1H-indole-7-carbonitrile 在 platinum(IV) oxide 、 palladium on activated charcoal manganese(IV) oxide 、 sodium hydroxide 、 氢气 、 双氧水 、 sodium hydride 、 溶剂黄146 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 二甲基亚砜 为溶剂， 反应 13.75h， 生成 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 、 sodium tetrahydroborate 、 tetrafluoroboric acid 、 硝酸 、 溶剂黄146 、 锌 、 sodium nitrite 作用下， 以 乙醇 、 溶剂黄146 、 N,N-二甲基甲酰胺 为溶剂， 反应 15.83h， 生成 1-acetyl-5-<1-(acetyloxy)-2-ethyl>-2,3-dihydro-1H-indole-7-carbonitrile
  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

• 5-Indolyl substituted aminoethanols
  申请人：American Home Products Corp.

  公开号：US04521606A1

  公开（公告）日：1985-06-04

  Herein is disclosed bicyclic-substituted aminoethanol derivatives, therapeutically acceptable acid addition salts thereof, processes for their preparation, methods of using the derivatives and pharmaceutical compositions. The derivatives are useful for treating hypertension in a mammal.

  本文披露了双环取代氨基乙醇衍生物，其治疗可接受的酸盐，其制备过程，衍生物的使用方法和制药组合物。这些衍生物可用于治疗哺乳动物的高血压。
• ASSELIN, A. A.;CROSILLA, D. A.;HUMBER, L. G.
  作者：ASSELIN, A. A.、CROSILLA, D. A.、HUMBER, L. G.

  DOI：——

  日期：——
• 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：——
• ——
  作者：ASSELIN A. A.、 CROSILLA D. A.、 HUMBER L. G.

  DOI：——

  日期：——
• US4521606A
  申请人：——

  公开号：US4521606A

  公开（公告）日：1985-06-04