1-phenyl-8-(3-phenylpropyl)-1,3,8-triazaspiro[4.5]decan-4-one | 1050-54-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑烷类
• 英文名称: 1-phenyl-8-(3-phenylpropyl)-1,3,8-triazaspiro[4.5]decan-4-one
• 英文别名: 1-phenyl-8-(3-phenyl-propyl)-1,3,8-triaza-spiro[4.5]decan-4-one
• CAS: 1050-54-0
• 化学式: C₂₂H₂₇N₃O
• 分子量: 349.476
• InChiKey: DWZMSKKFIPPHML-UHFFFAOYSA-N

物化性质

• 熔点：
  169.6-170.8 °C
• 沸点：
  577.9±50.0 °C(Predicted)
• 密度：
  1.18±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  26
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  35.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  3-苯丙醇 、 1-苯基-1,3,8-三唑螺环(4,5)十烷-4-酮 在 N,N-二异丙基乙胺 、 (cyanomethyl)trimethylphosphonium iodide 作用下， 以 various solvent(s) 为溶剂， 反应 2.0h， 以80%的产率得到1-phenyl-8-(3-phenylpropyl)-1,3,8-triazaspiro[4.5]decan-4-one
  参考文献：
  名称：

  (Cyanomethyl)trialkylphosphonium Iodides:  Efficient Reagents for the Intermolecular Alkylation of Amines with Alcohols in Solution and on Solid Phase

  摘要：

  DOI：

  10.1021/jo001735p

文献信息

• Antagonism of 1-(2,5-dimethoxy-4-methylphenyl)-2-aminopropane stimulus with a newly identified 5-HT2- versus 5-HT1C-selective antagonist
  作者：Abd M. Ismaiel、Joseph De Los Angeles、Milt Teitler、Stacy Ingher、Richard A. Glennon

  DOI：10.1021/jm00069a010

  日期：1993.8

  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.
• (Cyanomethyl)trialkylphosphonium Iodides:  Efficient Reagents for the Intermolecular Alkylation of Amines with Alcohols in Solution and on Solid Phase
  作者：Florencio Zaragoza、Henrik Stephensen

  DOI：10.1021/jo001735p

  日期：2001.4.1