2-[3-(4-fluorophenoxy)propyl]-1H-isoindole-1,3(2H)-dione | 253443-45-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 英文名称: 2-[3-(4-fluorophenoxy)propyl]-1H-isoindole-1,3(2H)-dione
• 英文别名: N-((3-(4-Fluorophenoxy)Propyl))Phthalimide；2-(3-(4-Fluorophenoxy)propyl)isoindoline-1,3-dione；2-[3-(4-fluorophenoxy)propyl]isoindole-1,3-dione
• CAS: 253443-45-7
• 化学式: C₁₇H₁₄FNO₃
• 分子量: 299.301
• InChiKey: MRACCTNAKUEABU-UHFFFAOYSA-N

物化性质

• 沸点：
  458.1±25.0 °C(Predicted)
• 密度：
  1.305±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  46.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-[3-(4-fluorophenoxy)propyl]-1H-isoindole-1,3(2H)-dione 在 一水合肼 作用下， 以 乙醇 为溶剂， 反应 3.0h， 以93%的产率得到3-(4-氟苯氧基)-1-丙胺
  参考文献：
  名称：

  Antagonism of 1-(2,5-dimethoxy-4-methylphenyl)-2-aminopropane stimulus with a newly identified 5-HT2- versus 5-HT1C-selective antagonist

  摘要：

  DOM [i.e., 1-(2,5-dimethoxy-4-methylphenyl)-2-aminopropane] is a 5-HT1C/2 serotonin agonist that exerts stimulus control of behavior in animals. In order to determine if the discriminative stimulus effect of DOM is 5-HT1C- or 5-HT2-mediated, it would be informative to conduct tests of stimulus antagonism with a 5-HT1C- or 5-HT2-selective antagonist. To date, no such agents exist. Although the neuroleptic agent spiperone binds at D2 dopamine receptors and 5-HT1A serotonin receptors, (a) it displays about a 1000-fold selectivity for 5-HT2 versus 5-HT1C sites and (b) it has been used as a ''5-HT2-selective'' antagonist. Because spiperone is a behaviorally disruptive agent, it is not suitable for use in drug-discrimination studies. Using the spiperone molecule as a starting point, a limited structure-affinity investigation was conducted in order to identify a suitable antagonist with high affinity and selectivity for 5-HT2 receptors, and yet an antagonist that might lack the disruptive actions of spiperone. Various modifications of the spiperone molecule were examined, but most resulted in decreased 5-HT2 affinity or in loss of selectivity. One compound, 8-[3-(4-fluorophenoxy)propyl]-1-phenyl-1,3,8-triazaspiro[4.5]decan-4-one(26), was shown to bind at 5-HT2 sites with high affinity (K(i) = 2 nM) and >2,000-fold selectivity versus 5-HT1C sites. In tests of stimulus antagonism using rats trained to discriminate 1 mg/kg of DOM from saline vehicle, 26 behaved as a potent antagonist (ED50 = 0.003 mg/kg) and lacked the disruptive effects associated with spiperone. As such, (a) it would appear that the DOM stimulus is primarily a 5-HT2-mediated, and not 5-HT1C-mediated, phenomenon, and (b) compound 26 may find application in other pharmacologic investigations where spiperone may not be a suitable antagonist.

  DOI：

  10.1021/jm00069a010
• 作为产物：
  描述：

  4-氟苯酚 、 N-(3-溴丙基)苯二胺 在 magnesium sulfate 、 potassium carbonate 作用下， 以 正己烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 2-[3-(4-fluorophenoxy)propyl]-1H-isoindole-1,3(2H)-dione
  参考文献：
  名称：

  5-HT7 receptor antagonists

  摘要：

  本发明涉及具有对5-HT7受体的药理活性的化合物。描述了用于治疗中枢神经系统疾病的药物组合物和使用它们的方法。

  公开号：

  US06239143B1

文献信息

• Amidopropoxyphenyl Orexin Receptor Antagonists
  申请人：Coleman Paul J.

  公开号：US20080262046A1

  公开（公告）日：2008-10-23

  The present invention is directed to amidopropoxyphenyl compounds which are antagonists of orexin receptors, and which are useful in the treatment or prevention of neurological and psychiatric disorders and diseases in which orexin receptors are involved. The invention is also directed to pharmaceutical compositions comprising these compounds and the use of these compounds and compositions in the prevention or treatment of such diseases in which orexin receptors are involved.

  本发明涉及对嗪类受体拮抗剂的氨基丙氧基苯基化合物，适用于治疗或预防涉及嗪类受体的神经系统和精神疾病和疾病。本发明还涉及包含这些化合物的制药组合物以及这些化合物和组合物在预防或治疗涉及嗪类受体的这些疾病中的用途。
• WO2006/110626
  申请人：——

  公开号：——

  公开（公告）日：——
• US6239143B1
  申请人：——

  公开号：US6239143B1

  公开（公告）日：2001-05-29
• US6486173B2
  申请人：——

  公开号：US6486173B2

  公开（公告）日：2002-11-26
• [EN] 5-HT7 RECEPTOR ANTAGONISTS<br/>[FR] ANTAGONISTES DU RECEPTEUR 5-HT7
  申请人：DU PONT PHARM CO

  公开号：WO2000000472A1

  公开（公告）日：2000-01-06

  The present invention relates to compounds of formula (I), of formula (II) or of formula (III) having pharmacological activity toward the 5-HT7 receptor. Pharmaceutical compositions and methods for their use in the treatment of CNS disorders are described.