4-(4-fluorobenzoyl)-1-[2-(4-iodo-2,5-dimethoxyphenyl)ethyl]piperidine | 692256-18-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-(4-fluorobenzoyl)-1-[2-(4-iodo-2,5-dimethoxyphenyl)ethyl]piperidine
• 英文别名: (4-Fluorophenyl)-[1-[2-(4-iodo-2,5-dimethoxyphenyl)ethyl]piperidin-4-yl]methanone
• CAS: 692256-18-1
• 化学式: C₂₂H₂₅FINO₃
• 分子量: 497.348
• InChiKey: QXUAXBVONPSMPB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  28
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  38.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4-(4-fluorobenzoyl)-1-[2-(4-iodo-2,5-dimethoxyphenyl)ethyl]piperidine 在 吡啶 、 盐酸羟胺 作用下， 以 乙醇 为溶剂， 反应 3.0h， 以92%的产率得到(4-fluorophenyl)-{1-[2-(4-iodo-2,5-dimethoxyphenyl)ethyl]piperidin-4-yl}methanone oxime hydrochloride
  参考文献：
  名称：

  4-(4-Fluorobenzoyl)-1-[2-(4-iodo-2,5-dimethoxyphenyl)ethyl]piperidine and its derivatives: synthesis and affinity at 5-HT2A, 5-HT2B and 5-HT2C serotonin receptors

  摘要：

  4-(4-Fluorobenzoyl)-1-[2-(4-iodo-2,5-dimethoxyphenyl)ethyl]piperidine (7) and its derivatives modified at the carbonyl group of the fluorobenzoyl moiety were prepared and evaluated for affinity at 5-HT2A, 5-HT2C (rat cortex) and 5-HT2B (rat stomach fundus) serotonin receptors. Compound 7 bound the 5-HT2A sites with higher affinity (K-i = 8.2 nM) than the 5-HT2B (K-b = 1 290 nM) and 5-HT2C ones (K-i = 54.2 nM). Modification of the benzoyl carbonyl group decreased the 5-HT2A and 5-HT2C affinities but did not significantly influence 5-HT2B affinity. This suggests that the carbonyl group is the determinant for the interaction with 5-HT2A and 5-HT2C receptor subtypes. Compound 7 was found to be a 5-HT2A receptor antagonist. (C) 1999 Editions scientifiques et medicales Elsevier SAS.

  DOI：

  10.1016/s0223-5234(99)00208-1
• 作为产物：
  描述：

  2-(4-iodo-2,5-dimethoxyphenyl)ethanol 在 吡啶 、 potassium carbonate 作用下， 以 丙酮 为溶剂， 反应 25.0h， 生成 4-(4-fluorobenzoyl)-1-[2-(4-iodo-2,5-dimethoxyphenyl)ethyl]piperidine
  参考文献：
  名称：

  4-(4-Fluorobenzoyl)-1-[2-(4-iodo-2,5-dimethoxyphenyl)ethyl]piperidine and its derivatives: synthesis and affinity at 5-HT2A, 5-HT2B and 5-HT2C serotonin receptors

  摘要：

  4-(4-Fluorobenzoyl)-1-[2-(4-iodo-2,5-dimethoxyphenyl)ethyl]piperidine (7) and its derivatives modified at the carbonyl group of the fluorobenzoyl moiety were prepared and evaluated for affinity at 5-HT2A, 5-HT2C (rat cortex) and 5-HT2B (rat stomach fundus) serotonin receptors. Compound 7 bound the 5-HT2A sites with higher affinity (K-i = 8.2 nM) than the 5-HT2B (K-b = 1 290 nM) and 5-HT2C ones (K-i = 54.2 nM). Modification of the benzoyl carbonyl group decreased the 5-HT2A and 5-HT2C affinities but did not significantly influence 5-HT2B affinity. This suggests that the carbonyl group is the determinant for the interaction with 5-HT2A and 5-HT2C receptor subtypes. Compound 7 was found to be a 5-HT2A receptor antagonist. (C) 1999 Editions scientifiques et medicales Elsevier SAS.

  DOI：

  10.1016/s0223-5234(99)00208-1