1-(1-acetyl-2,3-dihydro-1H-indol-5-yl)-2-ethanone | 101544-38-1

• 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: 1-(1-acetyl-2,3-dihydro-1H-indol-5-yl)-2-ethanone
• 英文别名: 1-(1-acetyl-2,3-dihydro-1H-indol-5-yl)-2-[bis(phenylmethyl)amino]-ethanone；1-(1-acetyl-2,3-dihydro-1H-indol-5-yl)-2-(bis(phenylmethyl)amino)ethanone；Ethanone, 1-(1-acetyl-2,3-dihydro-1H-indol-5-yl)-2-[bis(phenylmethyl)amino]-；1-(1-acetyl-2,3-dihydroindol-5-yl)-2-(dibenzylamino)ethanone
• CAS: 101544-38-1
• 化学式: C₂₆H₂₆N₂O₂
• mdl: MFCD14775348
• 分子量: 398.505
• InChiKey: CFIITSQYJZOTNN-UHFFFAOYSA-N

物化性质

• 熔点：
  130-130.5 °C(Solv: ethyl acetate (141-78-6))
• 沸点：
  637.2±55.0 °C(Predicted)
• 密度：
  1.192±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  30
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  40.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-(1-acetyl-2,3-dihydro-1H-indol-5-yl)-2-ethanone 在 吡啶 、 sodium tetrahydroborate 、 硝酸 、 溶剂黄146 、 锌 作用下， 以 乙醇 、 溶剂黄146 为溶剂， 反应 12.0h， 生成 1-acetyl-5-<1-(acetyloxy)-2-ethyl>-2,3-dihydro-1H-indole-7-amine
  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：

  N-乙酰基吲哚啉 在 三氯化铝 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 3.33h， 生成 1-(1-acetyl-2,3-dihydro-1H-indol-5-yl)-2-ethanone
  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。
• 5(Indolyl) and 5(2,3-dihydroindolyl) substituted aminoethanols and their
  申请人：American Home Products Corporation

  公开号：US04562200A1

  公开（公告）日：1985-12-31

  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.

  本发明公开了双环取代的氨基乙醇衍生物及其治疗上可接受的酸盐，其制备方法，使用衍生物的方法和制药组合物。该衍生物可用于治疗哺乳动物的高血压症。
• Bicyclo-heterocyclic nitrogen substituted aminoethanol derivatives
  申请人：American Home Products Corporation

  公开号：US04622399A1

  公开（公告）日：1986-11-11

  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.

  本发明公开了二环取代氨基乙醇衍生物、其治疗上可接受的酸盐、其制备方法、使用该衍生物的方法以及制备药物组合物的方法。该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：——