2-(4,5-Dihydro-1H-imidazol-2-yl)-1-phenyl-2,3-dihydro-1H-indole | 108797-02-0

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 2-(4,5-Dihydro-1H-imidazol-2-yl)-1-phenyl-2,3-dihydro-1H-indole
• 英文别名: dl-2,3-dihydro-2-(4,5-dihydroimidazol-2-yl)-1-phenylindole；2,3-Dihydro-2-(4,5-dihydroimidazol-2-yl)-1-phenylindole；2-(4,5-dihydro-1H-imidazol-2-yl)-1-phenyl-2,3-dihydroindole
• CAS: 108797-02-0
• 化学式: C₁₇H₁₇N₃
• 分子量: 263.342
• InChiKey: KJJIMWHJDMEMPM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  27.6
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-(4,5-Dihydro-1H-imidazol-2-yl)-1-phenyl-2,3-dihydro-1H-indole 生成 (E)-but-2-enedioic acid;2-(4,5-dihydro-1H-imidazol-2-yl)-1-phenyl-2,3-dihydroindole
  参考文献：
  名称：

  摘要：

  DOI：
• 作为产物：
  描述：

  ethyl 1-phenyl-1H-indole-2-carboxylate 在 三甲基铝 、 sodium cyanoborohydride 作用下， 以 甲苯 、 三氟乙酸 为溶剂， 反应 5.0h， 生成 2-(4,5-Dihydro-1H-imidazol-2-yl)-1-phenyl-2,3-dihydro-1H-indole
  参考文献：
  名称：

  Indoline analogs of idazoxan: potent .alpha.2-antagonists and .alpha.1-agonists

  摘要：

  The synthesis and alpha-adrenergic activity of a series of substituted 2-imidazolinylindolines are described. Substitution in the indoline ring generated compounds with a spectrum of adrenoceptor antagonist/agonist profiles that proved sensitive to both the nature and position of the substituent. Many of the derivatives possess greater presynaptic antagonist potency than the corresponding benzodioxan 1, dihydrobenzofuran 2, and indan 3 analogues; however, this alpha 2-antagonism is often accompanied by alpha 1-agonist activity. It was not possible to separate alpha 2-antagonist from alpha 1-agonist properties in this series. Compounds of most interest proved to be the N-ethyl 6, 5-chloro-N-methyl 18, and 5-chloro-N-ethyl 23 derivatives, all being potent alpha 2-antagonists and alpha 1-agonists. Substitution at the 4- and 7-position of the indoline ring generally gave compounds with nonselective agonist properties.

  DOI：

  10.1021/jm00400a009

文献信息

• 2,3-dihydro-2-(4,5-dihydroimidazol-2-yl)-indoles in composition form for
  申请人：Ciba-Geigy Corporation

  公开号：US04908376A1

  公开（公告）日：1990-03-13

  Compounds of the formula ##STR1## wherein each R is hydrogen or one R is hydrogen and the other is lower alkyl, R.sub.1 is hydrogen, lower alkyl, aryl, aralkyl or lower carboalkoxy, R.sub.2 is hydrogen or lower alkyl, and the ring A is unsubstituted or substituted by lower alkyl, lower alkoxy, halo or trifluoromethyl, and pharmaceutically acceptable salts thereof, their preparation, pharmaceutical compositions and the uses thereof, such as .alpha..sub.2 -adrenergic blocking agents, e.g. antidepressants, cognition enhancers and appetite suppressants, and as intraocular pressure reducing agents are disclosed.

  式为##STR1##的化合物，其中每个R是氢或一个R是氢而另一个是较低的烷基，R.sub.1是氢，较低的烷基，芳基，芳基烷基或较低的羰基烷氧基，R.sub.2是氢或较低的烷基，环A未取代或被较低的烷基，较低的烷氧基，卤素或三氟甲基取代，以及其药学上可接受的盐，其制备，药物组合物及其用途，例如α2-肾上腺素受体阻滞剂，如抗抑郁药，认知增强剂和食欲抑制剂，以及作为降低眼压的药剂。
• 2-(4,5-Dihydro-1H-imidazol-2-yl)-2,3-dihydroindole derivatives and their
  申请人：Synthelabo

  公开号：US04659731A1

  公开（公告）日：1987-04-21

  Derivatives of formula (I) ##STR1## in which X denotes a hydrogen or halogen atom, an alkoxy radical, an alkyl radical or an allyloxy radical, and R denotes a linear or branched alkyl radical, a cycloalkylalkyl radical, an alkenyl radical, an arylalkyl radical which can bear one or more substituents chosen from halogen atoms and methyl, methoxy and methylenedioxy radicals, or alternatively an optionally substituted phenyl radical, as well as the addition salts thereof with pharmaceutically acceptable acids produce an .alpha..sub.2 -receptor antagonist effect.

  (I)式的衍生物##STR1##其中X表示氢或卤原子，烷氧基，烷基或烯丙氧基，R表示线性或支链烷基，环烷烷基，烯丙基，苯基，可以带有一个或多个卤原子、甲基、甲氧基和亚甲二氧基基团的取代基，或者是一个可选择取代的苯基，以及其与药用酸的加合物产生α2-受体拮抗作用。
• 2,3-dihydro-2-(4,5-dihydroimidazol-2-yl)-indoles for reducing
  申请人：Ciba-Geigy Corporation

  公开号：US04912125A1

  公开（公告）日：1990-03-27

  Compounds of the formula ##STR1## wherein each R is hydrogen or one R is hydrogen and the other is lower alkyl, R.sub.1 is hydrogen, lower alkyl, aryl, aralkyl or lower carboalkoxy, R.sub.2 is hydrogen or lower alkyl, and the ring A is unsubstituted or substituted by lower alkyl, lower alkoxy, halo or trifluoromethyl, and pharmaceutically acceptable salts thereof, their preparation, pharmaceutical compositions and the uses thereof, such as .alpha..sub.2 -adrenergic blocking agents, e.g. antidepressants, cognition enhancers and appetite supressants, and as intraocular pressure reducing agents are disclosed.

  本发明公开了化学式为##STR1##的化合物，其中每个R是氢或一个R是氢，另一个是较低的烷基，R.sub.1是氢，较低的烷基，芳基，芳基烷基或较低的羧基烷氧基，R.sub.2是氢或较低的烷基，环A未经取代或被较低的烷基，较低的烷氧基，卤素或三氟甲基取代，以及其药学上可接受的盐，其制备，制药组合物和用途，例如作为α2-肾上腺素能阻断剂，例如抗抑郁剂，认知增强剂和食欲抑制剂，以及作为降低眼内压的剂。
• .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.
• HUEBNER, CHARLES F.;FRANCIS, JOHN E.
  作者：HUEBNER, CHARLES F.、FRANCIS, JOHN E.

  DOI：——

  日期：——