(3-chloromethyl-phenyl)-(2,3-dihydro-indol-1-yl)-methanone | 167024-09-1

• 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: (3-chloromethyl-phenyl)-(2,3-dihydro-indol-1-yl)-methanone
• 英文别名: N-(3-(chloromethyl)benzoyl)indoline；[3-(Chloromethyl)phenyl]-(2,3-dihydroindol-1-yl)methanone
• CAS: 167024-09-1
• 化学式: C₁₆H₁₄ClNO
• mdl: MFCD12540812
• 分子量: 271.746
• InChiKey: ZKLPQWVERHDLHR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.187
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1-(2-isopropoxyphenyl)-piperazine fumarate 、 (3-chloromethyl-phenyl)-(2,3-dihydro-indol-1-yl)-methanone 以 四氢呋喃 为溶剂， 生成 (2,3-Dihydro-indol-1-yl)-{3-[4-(2-isopropoxy-phenyl)-piperazin-1-ylmethyl]-phenyl}-methanone
  参考文献：
  名称：

  Orally Active Benzamide Antipsychotic Agents with Affinity for Dopamine D₂, Serotonin 5-HT_1A, and Adrenergic α₁ Receptors

  摘要：

  New antipsychotic drugs are needed because current therapy is ineffective for many schizophrenics and because treatment is often accompanied by extrapyramidal symptoms and dyskinesias. This paper describes the design, synthesis, and evaluation of a series of related (aminomethyl)benzamides in assays predictive of antipsychotic activity in humans. These compounds had notable affinity for dopamine D-2, serotonin 5-HT1A, and alpha(1)-adrenergic receptors. The arylpiperazine 1-[3-[[4-[2-(1-methylethoxy)phenyl]-1-piperazinyl]methyl]benzoyl]piperidine (mazapertine, 6) was chosen because of its overall profile for evaluation in human clinical trials. The corresponding 4-arylpiperidine derivative 67 was also highly active indicating that the aniline nitrogen of 6 is not required for activity. Other particularly active structures include homopiperidine amide 14 and N-methylcyclohexylamide 31.

  DOI：

  10.1021/jm970164z
• 作为产物：
  描述：

  吲哚啉 、 3-(氯甲基)苯甲酰氯 在 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 生成 (3-chloromethyl-phenyl)-(2,3-dihydro-indol-1-yl)-methanone
  参考文献：
  名称：

  Orally Active Benzamide Antipsychotic Agents with Affinity for Dopamine D₂, Serotonin 5-HT_1A, and Adrenergic α₁ Receptors

  摘要：

  New antipsychotic drugs are needed because current therapy is ineffective for many schizophrenics and because treatment is often accompanied by extrapyramidal symptoms and dyskinesias. This paper describes the design, synthesis, and evaluation of a series of related (aminomethyl)benzamides in assays predictive of antipsychotic activity in humans. These compounds had notable affinity for dopamine D-2, serotonin 5-HT1A, and alpha(1)-adrenergic receptors. The arylpiperazine 1-[3-[[4-[2-(1-methylethoxy)phenyl]-1-piperazinyl]methyl]benzoyl]piperidine (mazapertine, 6) was chosen because of its overall profile for evaluation in human clinical trials. The corresponding 4-arylpiperidine derivative 67 was also highly active indicating that the aniline nitrogen of 6 is not required for activity. Other particularly active structures include homopiperidine amide 14 and N-methylcyclohexylamide 31.

  DOI：

  10.1021/jm970164z

文献信息

• Dihydroindolyl methanones as alpha 1a/1d adrenoreceptor modulators for the treatment of benign prostatic hypertrophy and lower urinary tract symptoms
  申请人：Baxter W. Ellen

  公开号：US20060183902A1

  公开（公告）日：2006-08-17

  The present invention relates to new compounds of Formula (I): and pharmaceutically acceptable forms thereof, use of the compounds as α 1a and/or α 1d adrenoreceptor modulators, including use of a pharmaceutical composition, medicine or medicament comprising said compounds, a process to prepare said compounds and a method for treating an α 1a and/or α 1d adrenoreceptor mediated disorder.

  本发明涉及公式（I）的新化合物及其药用可接受形式，所述化合物用作α1a和/或α1d肾上腺受体调节剂，包括使用含有该化合物的药物组合物、药品或药剂，制备该化合物的过程以及治疗α1a和/或α1d肾上腺受体介导的疾病的方法。
• Hindered rotation congeners of mazapertine: High affinity ligands for the 5-HT1A receptor
  作者：Ellen W. Baxter、Allen B. Reitz

  DOI：10.1016/s0960-894x(97)00074-7

  日期：1997.1

  Hindered rotation analogs of the antipsychotic mazapertine (1) were prepared. These compounds exhibited high affinity for the 5-HT1A receptor, but not for other serotonin or dopamine receptors. The related beta-carboline structures were also synthesized and were found to be potent 5-HT1A ligands. (C) 1997 Elsevier Science Ltd.
• TRICYCLIC COMPOUNDS HAVING AFFINITY FOR THE 5-HT1A RECEPTOR
  申请人：ORTHO PHARMACEUTICAL CORPORATION

  公开号：EP0746556B1

  公开（公告）日：2002-09-25
• US5512566A
  申请人：——

  公开号：US5512566A

  公开（公告）日：1996-04-30
• [EN] TRICYCLIC COMPOUNDS HAVING AFFINITY FOR THE 5-HT1A RECEPTOR<br/>[FR] COMPOSES TRICYCLIQUES AYANT UNE AFFINITE POUR LE RECEPTEUR DE 5-HT1A
  申请人：ORTHO PHARMACEUTICAL CORPORATION

  公开号：WO1995011903A1

  公开（公告）日：1995-05-04

  (EN) Compounds represented by general formula (I) having affinity for the 5-HT1A receptor are disclosed as useful in treating diseases of the central nervous system.(FR) L'invention décrit des composés représentés par la formule générale (I), qui présentent une affinité pour le récepteur de la 5-HT1A. Ces composés sont utiles pour le traitement des maladies du système nerveux central.