ethyl 1-n-butyl-2,3-dihydro-1H-indolecarboxylate | 108797-64-4

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: ethyl 1-n-butyl-2,3-dihydro-1H-indolecarboxylate
• 英文别名: Ethyl 1-butyl-2,3-dihydroindole-2-carboxylate
• CAS: 108797-64-4
• 化学式: C₁₅H₂₁NO₂
• 分子量: 247.337
• InChiKey: OUDCKTODFMIIJC-UHFFFAOYSA-N

物化性质

• 沸点：
  352.4±30.0 °C(Predicted)
• 密度：
  1.055±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  18
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  ethyl 1-n-butyl-2,3-dihydro-1H-indolecarboxylate 在 三甲基铝 乙二胺 作用下， 以 乙醇 、 水 、 甲苯 、 Petroleum ether 为溶剂， 生成 2-(4,5-dihydro-2-1H-imidazolyl)-1-n-butyl-2,3-dihydro-1H-indole
  参考文献：
  名称：

  .alpha..sub.2 antagonistic

  摘要：

  吲哚衍生物，以盘旋体或旋光异构体的形式存在，其化学式为（I）其中R.sub.1是氢原子，线性或支链（C.sub.1-6）烷基基团，（C.sub.3-6）环烷基-(C.sub.1-4)烷基基团，（C.sub.2-6）烯基基团，萘甲基基团，苯乙基基团或苄基基团，可选择地被一个或多个卤素原子或甲基、甲氧基或亚甲二氧基基团取代，且R.sub.2为H或（C.sub.1-4）烷基或烯丙基基团，以及它们的药学上可接受的盐；是α2-拮抗剂，可用于治疗抑郁症、低血压、术后麻痹性肠梗阻、哮喘和肥胖症。

  公开号：

  US04598086A1
• 作为产物：
  描述：

  吲哚-2-羧酸乙酯 在 三乙基硅烷 、 sodium hydride 作用下， 以 三氟乙酸 为溶剂， 反应 3.33h， 生成 ethyl 1-n-butyl-2,3-dihydro-1H-indolecarboxylate
  参考文献：
  名称：

  .alpha.2-Adrenergic agonists/antagonists: the synthesis and structure-activity relationships of a series of indolin-2-yl and tetrahydroquinolin-2-yl imidazolines

  摘要：

  The synthesis and alpha 2-adrenergic activity of a series of indolin-2-yl and tetrahydroquinolin-2-yl imidazolines are described. The indolin-2-yl imidazoline 4b was found to possess potent alpha 2-adrenergic agonist and antagonist activity. The modification of the substituents on the indoline ring of 4b has led to the separation of these activities. Substitution on the aromatic ring of 4b with halogen or increasing the size of the N-alkyl substituent of 4b gave alpha 2-adrenergic antagonists without agonist activity. The N-allylindoline 4d is more potent than idazoxan in vitro and is equipotent in vivo, but is less receptor selective (alpha 2 vs. alpha 1) than idazoxan. The cis-1,3-dimethylindolin-2-yl imidazoline 6a is an alpha 2-adrenergic agonist equal in potency to clonidine in vitro, while the trans-1,3-dimethylindolin-2-yl imidazoline 6b is a moderately potent alpha 2-adrenergic antagonist.

  DOI：

  10.1021/jm00392a005

文献信息

• BIGG, D.;MENIN, J.
  作者：BIGG, D.、MENIN, J.

  DOI：——

  日期：——
• HLASTA, DENNIS J.;LUTTINGER, DANIEL;PERRONE, MARK H.;SILBERNAGEL, MARLA J+, J. MED. CHEM., 30,(1987) N 9, 1555-1562
  作者：HLASTA, DENNIS J.、LUTTINGER, DANIEL、PERRONE, MARK H.、SILBERNAGEL, MARLA J+

  DOI：——

  日期：——
• .alpha.2-Adrenergic agonists/antagonists: the synthesis and structure-activity relationships of a series of indolin-2-yl and tetrahydroquinolin-2-yl imidazolines
  作者：Dennis J. Hlasta、Daniel Luttinger、Mark H. Perrone、Marla J. Silbernagel、Susan J. Ward、Dean R. Haubrich

  DOI：10.1021/jm00392a005

  日期：1987.9

  The synthesis and alpha 2-adrenergic activity of a series of indolin-2-yl and tetrahydroquinolin-2-yl imidazolines are described. The indolin-2-yl imidazoline 4b was found to possess potent alpha 2-adrenergic agonist and antagonist activity. The modification of the substituents on the indoline ring of 4b has led to the separation of these activities. Substitution on the aromatic ring of 4b with halogen or increasing the size of the N-alkyl substituent of 4b gave alpha 2-adrenergic antagonists without agonist activity. The N-allylindoline 4d is more potent than idazoxan in vitro and is equipotent in vivo, but is less receptor selective (alpha 2 vs. alpha 1) than idazoxan. The cis-1,3-dimethylindolin-2-yl imidazoline 6a is an alpha 2-adrenergic agonist equal in potency to clonidine in vitro, while the trans-1,3-dimethylindolin-2-yl imidazoline 6b is a moderately potent alpha 2-adrenergic antagonist.
• .alpha..sub.2 antagonistic
  申请人：——

  公开号：US04598086A1

  公开（公告）日：1986-07-01

  Indole derivatives, in the form of racemates or optically active isomers, of the formula (I) ##STR1## in which R.sub.1 is a hydrogen atom, a linear or branched (C.sub.1-6) alkyl group, a (C.sub.3-6) cycloalkyl-(C.sub.1-4) alkyl group, a (C.sub.2-6) alkenyl group, the naphthylmethyl group, the phenethyl group or a benzyl group optionally substituted by one or more halogen atom or methyl, methoxyl or methylenedioxy group and R.sub.2 is H or a (C.sub.1-4) alkyl or allyl group, and their pharmaceutically acceptable salts; are .alpha..sub.2 -antagonists and useful for the treatment of depression, hypotension, post-operative paralytic ileum, asthma and obesity.

  吲哚衍生物，以盘旋体或旋光异构体的形式存在，其化学式为（I）其中R.sub.1是氢原子，线性或支链（C.sub.1-6）烷基基团，（C.sub.3-6）环烷基-(C.sub.1-4)烷基基团，（C.sub.2-6）烯基基团，萘甲基基团，苯乙基基团或苄基基团，可选择地被一个或多个卤素原子或甲基、甲氧基或亚甲二氧基基团取代，且R.sub.2为H或（C.sub.1-4）烷基或烯丙基基团，以及它们的药学上可接受的盐；是α2-拮抗剂，可用于治疗抑郁症、低血压、术后麻痹性肠梗阻、哮喘和肥胖症。