(2,3-dimethoxyphenyl)-(1-(p-fluorobenzyl)-piperidin-4-yl)-methanol | 1160298-46-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: (2,3-dimethoxyphenyl)-(1-(p-fluorobenzyl)-piperidin-4-yl)-methanol
• 英文别名: (2,3-Dimethoxyphenyl)-(1-(p-fluorobenzyl)-piperidine-4-yl)-methanol；(2,3-dimethoxyphenyl)-[1-[(4-fluorophenyl)methyl]piperidin-4-yl]methanol
• CAS: 1160298-46-3
• 化学式: C₂₁H₂₆FNO₃
• 分子量: 359.441
• InChiKey: ACARRFRVNJRYJL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  26
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  41.9
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  4-氟溴苄 、 外消旋(2,3-二甲氧基苯基)- 在 碳酸氢钠 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.5h， 以58%的产率得到(2,3-dimethoxyphenyl)-(1-(p-fluorobenzyl)-piperidin-4-yl)-methanol
  参考文献：
  名称：

  Synthesis and in vitro affinities of various MDL 100907 derivatives as potential 18F-radioligands for 5-HT2A receptor imaging with PET

  摘要：

  Radiolabelled piperidine derivatives such as [C-11] MDL 100907 and [F-18] altanserin have played an important role in diagnosing malfunction in the serotonergic neurotransmission. A variety of novel piperidine MDL 100907 derivatives, possible to label with F-18-fluorine, were synthesized to improve molecular imaging properties of [C-11] MDL 100907. Their in vitro affinities to a broad spectrum of neuroreceptors and their lipophilicities were determined and compared to the clinically used reference compounds MDL 100907 and altanserin. The novel compounds MA-1 (53) and (R)-MH.MZ (56) show K-i-values in the nanomolar range towards the 5-HT2A receptor and insignificant binding to other 5-HT receptor sub-types or receptors. Interestingly, compounds MA-1 (53), MH.MZ (55) and (R)-MH.MZ (56) provide a receptor selectivity pro. le similar to MDL 100907. These compounds could possibly be preferable antagonistic F-18-tracers for visualization of the 5-HT2A receptor status. Medium affine compounds (VK-1 (32), (51), (52), (54)) were synthesized and have K-i values between 30 and 120 nM. All promising compounds show logP values between 2 and 3, that is, within the range of those for the established radiotracers altanserin and MDL 100907. The novel compounds MA-1 (53) and (R)-MH.MZ (56) thus appear to be promising high affine and selective tracers of F-18-labelled analogues for 5-HT2A imaging with PET. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2009.03.021

文献信息

• Synthesis and in vitro affinities of various MDL 100907 derivatives as potential 18F-radioligands for 5-HT2A receptor imaging with PET
  作者：Matthias M. Herth、Vasko Kramer、Markus Piel、Mikael Palner、Patrick J. Riss、Gitte M. Knudsen、Frank Rösch

  DOI：10.1016/j.bmc.2009.03.021

  日期：2009.4

  Radiolabelled piperidine derivatives such as [C-11] MDL 100907 and [F-18] altanserin have played an important role in diagnosing malfunction in the serotonergic neurotransmission. A variety of novel piperidine MDL 100907 derivatives, possible to label with F-18-fluorine, were synthesized to improve molecular imaging properties of [C-11] MDL 100907. Their in vitro affinities to a broad spectrum of neuroreceptors and their lipophilicities were determined and compared to the clinically used reference compounds MDL 100907 and altanserin. The novel compounds MA-1 (53) and (R)-MH.MZ (56) show K-i-values in the nanomolar range towards the 5-HT2A receptor and insignificant binding to other 5-HT receptor sub-types or receptors. Interestingly, compounds MA-1 (53), MH.MZ (55) and (R)-MH.MZ (56) provide a receptor selectivity pro. le similar to MDL 100907. These compounds could possibly be preferable antagonistic F-18-tracers for visualization of the 5-HT2A receptor status. Medium affine compounds (VK-1 (32), (51), (52), (54)) were synthesized and have K-i values between 30 and 120 nM. All promising compounds show logP values between 2 and 3, that is, within the range of those for the established radiotracers altanserin and MDL 100907. The novel compounds MA-1 (53) and (R)-MH.MZ (56) thus appear to be promising high affine and selective tracers of F-18-labelled analogues for 5-HT2A imaging with PET. (C) 2009 Elsevier Ltd. All rights reserved.