1,3,8-三氮杂螺[4.5]癸烷-4-酮,8-[4-(4-氟苯基)-4-羰基丁基]-3-[(2-硝基苯基)甲基]-1-苯基- | 138091-78-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 1,3,8-三氮杂螺[4.5]癸烷-4-酮,8-[4-(4-氟苯基)-4-羰基丁基]-3-[(2-硝基苯基)甲基]-1-苯基-
• 英文名称: 8-[4-(4-Fluoro-phenyl)-4-oxo-butyl]-3-(2-nitro-benzyl)-1-phenyl-1,3,8-triaza-spiro[4.5]decan-4-one
• 英文别名: 8-[4-(4-fluorophenyl)-4-oxobutyl]-3-[(2-nitrophenyl)methyl]-1-phenyl-1,3,8-triazaspiro[4.5]decan-4-one
• CAS: 138091-78-8
• 化学式: C₃₀H₃₁FN₄O₄
• 分子量: 530.599
• InChiKey: DOYHXPOZCLMQII-UHFFFAOYSA-N

物化性质

• 沸点：
  736.1±60.0 °C(Predicted)
• 密度：
  1.34±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  39
• 可旋转键数：
  8
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  89.7
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  螺哌隆 、 alkaline earth salt of/the/ methylsulfuric acid 在 sodium hydride 作用下， 生成 1,3,8-三氮杂螺[4.5]癸烷-4-酮,8-[4-(4-氟苯基)-4-羰基丁基]-3-[(2-硝基苯基)甲基]-1-苯基-
  参考文献：
  名称：

  Effect of N-alkylation on the affinities of analogs of spiperone for dopamine D2 and serotonin 5-HT2 receptors

  摘要：

  Two series of N-substituted spiperone analogues were prepared and evaluated in vitro to measure their affinities for dopamine D2 and serotonin 5-HT2 receptors. Substitution of the amide nitrogen with an alkyl group of five carbon units or less resulted in analogues displaying a low selectivity for D2 compared to 5-HT2 receptors. However, a moderate improvement in selectivity for D2 receptors was observed with N-benzylspiperone. Substitution at either the ortho or para position of the benzyl group resulted in a further reduction in affinity for 5-HT2 receptors and improvement in the selectivity ratio. Examination of N-substituted analogues of spiperone may provide insights into the topography of the antagonist binding region of the 5-HT2 receptor. The results also suggest that an F-18-labeled analogue of N-(4-nitrobenzyl)spiperone (4p) may be a suitable tracer for studying D2 receptors with positron emission tomography since this compound displays a high selectivity for D2 receptors relative to that of spiperone and N-methylspiperone.

  DOI：

  10.1021/jm00081a002

文献信息

• Effect of N-alkylation on the affinities of analogs of spiperone for dopamine D2 and serotonin 5-HT2 receptors
  作者：Robert H. Mach、Joseph R. Jackson、Robert R. Luedtke、Kathryn J. Ivins、Perry B. Molinoff、Richard L. Ehrenkaufer

  DOI：10.1021/jm00081a002

  日期：1992.2

  Two series of N-substituted spiperone analogues were prepared and evaluated in vitro to measure their affinities for dopamine D2 and serotonin 5-HT2 receptors. Substitution of the amide nitrogen with an alkyl group of five carbon units or less resulted in analogues displaying a low selectivity for D2 compared to 5-HT2 receptors. However, a moderate improvement in selectivity for D2 receptors was observed with N-benzylspiperone. Substitution at either the ortho or para position of the benzyl group resulted in a further reduction in affinity for 5-HT2 receptors and improvement in the selectivity ratio. Examination of N-substituted analogues of spiperone may provide insights into the topography of the antagonist binding region of the 5-HT2 receptor. The results also suggest that an F-18-labeled analogue of N-(4-nitrobenzyl)spiperone (4p) may be a suitable tracer for studying D2 receptors with positron emission tomography since this compound displays a high selectivity for D2 receptors relative to that of spiperone and N-methylspiperone.