[3-O-methyl-11C]-(R)-(+)-4-(1-hydroxy-1-(2,3-dimethoxyphenyl)methyl)-N-2-(4-fluorophenylethyl)piperidine | 174792-03-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: [3-O-methyl-11C]-(R)-(+)-4-(1-hydroxy-1-(2,3-dimethoxyphenyl)methyl)-N-2-(4-fluorophenylethyl)piperidine
• 英文别名: (R)-(+)-α-(2-methoxy-3-[11C]methoxyphenyl)-1-[2-(4-fluorophenyl)ethyl]-4-piperidinemethanone；[11C]-(R)-(+)-4-(1-hydroxy-1-(2,3-dimethoxyphenyl)methyl)-N-2-(4-fluorophenylethyl)piperidine；[¹¹C]MDL100907；(R)-(+)-[3-OCH3-11C]MDL；Volinanserin C-11；(R)-[1-[2-(4-fluorophenyl)ethyl]piperidin-4-yl]-(2-methoxy-3-(111C)methoxyphenyl)methanol
• CAS: 174792-03-1
• 化学式: C₂₂H₂₈FNO₃
• 分子量: 372.457
• InChiKey: HXTGXYRHXAGCFP-AVUPQLEMSA-N

物化性质

• 密度：
  1.151±0.06 g/cm3(Temp: 25 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  27
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.45
• 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：

  (alphaR)-1-[2-(4-氟苯基)乙基]-alpha-(3-羟基-2-甲氧基苯基)-4-哌啶甲醇 、 alkaline earth salt of/the/ methylsulfuric acid 在 sodium hydroxide 作用下， 以 丙酮 为溶剂， 反应 0.05h， 生成 [3-O-methyl-11C]-(R)-(+)-4-(1-hydroxy-1-(2,3-dimethoxyphenyl)methyl)-N-2-(4-fluorophenylethyl)piperidine
  参考文献：
  名称：

  [11C] MDL 100907，一种放射性正电子，用于通过正电子发射断层扫描对5-HT（2A）受体进行选择性成像。

  摘要：

  高选择性5-HT2A受体拮抗剂MDL 100907（（R）-（+）-4-（1-羟基-1-（2,3-二甲氧基苯基）甲基）-N -2-（4-氟苯基乙基）哌啶）被标记为11C，用于正电子发射断层扫描（PET）研究。在食蟹猴中静脉内注射（R）-（+）-[3-OCH3-11C] MDL 100907 [11C] MDL 100907）后，以新皮层与小脑的比例获得了富含5-HT2A受体的新皮层区域的明显积累。 60-80分钟后的3.5-4.5。在新皮层区域，在40-60分钟内发生了短暂的平衡。注射酮色林后，新皮层中的放射性降低，但小脑中的放射性降低，这表明注射[11C] MDL 100907后的新皮层放射性代表与5-HT2A受体的特异性结合。

  DOI：

  10.1016/0024-3205(96)00013-6

文献信息

• An efficient synthesis of the precursors of [11C]MDL 100907 labeled in two specific positions
  作者：Yiyun Huang、Khalid Mahmood、Chester A. Mathis

  DOI：10.1002/(sici)1099-1344(199910)42:10<949::aid-jlcr253>3.0.co;2-s

  日期：1999.10

  An efficient, integrated route for the synthesis of two precursors of [C-11]MDL 100907 labeled in the 2'- or 3'-methoxy position is reported. The synthesis involved a one-pot, two-step process to transform the intermediate esters to ketones and subsequent resolution of the racemic alcohols to their respective enantiomers. The resolved, enantiomerically pure phenol precursors were reacted with high specific activity [C-11]methyl iodide to produce [C-11]MDL 100907 labeled in two specific positions.
• Lundkvist, C.; Sandell, J.; Nagren, K., Journal of labelled compounds and radiopharmaceuticals, 1997, vol. 40, p. 583 - 585
  作者：Lundkvist, C.、Sandell, J.、Nagren, K.、Pike, V. W.、Swahn, C.-G.、et al.

  DOI：——

  日期：——
• Improved syntheses of the PET radioligands, [11C]FLB 457, [11C]MDL 100907 and [11C]β-CIT-FE, by the use of [11C]methyl triflate
  作者：Camilla Lundkvist、Johan Sandell、Kjell Någren、Victor W. Pike、Christer Halldin

  DOI：10.1002/(sici)1099-1344(199806)41:6<545::aid-jlcr99>3.0.co;2-7

  日期：1998.6

  The highly reactive labelling agent,[C-11]methyl triflate, was used to synthesise three recently developed PET radioligands. The labelling reactions were C-11-methylations of phenols for the preparations of the D-2 receptor radioligand, [C-11]FLB 457, and the 5-MT2A receptor radioligand, [C-11]MDL 100907, and C-11-methylation of a carboxylic acid for the preparation of the dopamine transporter radioligand, [C-11]beta-CIT-FE. The synthesis of the 5-MT1A receptor radioligand, [O-methyl-C-11]WAY-100635, was used to establish general reaction conditions for the methylation of phenols with [C-11]methyl triflate. Compared to the previous use of [C-11]methyl iodide in these radiosyntheses, [C-11]methyl triflate demanded less precursor, allowed faster reactions and improved radiochemical yields. Normal-phase HPLC was used to speed up product purifications (except for [C-11]beta-CIT-FE). Hence, preparation times were shorter, resulting in radioligands with higher specific radioactivity.
• [11C]MDL 100907, a radioligand for selective imaging of 5-HT2A receptors with positron emission tomography
  作者：Camilla Lundkvist、Christer Halldin、Nathalie Ginovart、Svante Nyberg、Carl-Gunnar Swahn、Albert A. Carr、Francoise Brunner、Lars Farde

  DOI：10.1016/0024-3205(96)00013-6

  日期：1996.2

  The highly selective 5-HT2A receptor antagonist, MDL 100907 ((R)-(+)-4 -(l-hydroxy-1-(2,3-dimethoxyphenyl)methyl)-N -2-(4-fluorophenylethyl)piperidine), was labeled with 11C for Positron Emission Tomography (PET) studies. After i.v. injection of (R)-(+)-[3-OCH3-11C]MDL 100907 [11C]MDL 100907) in Cynomolgus monkeys a marked accumulation in the 5-HT2A receptor rich neocortical regions was obtained with

  高选择性5-HT2A受体拮抗剂MDL 100907（（R）-（+）-4-（1-羟基-1-（2,3-二甲氧基苯基）甲基）-N -2-（4-氟苯基乙基）哌啶）被标记为11C，用于正电子发射断层扫描（PET）研究。在食蟹猴中静脉内注射（R）-（+）-[3-OCH3-11C] MDL 100907 [11C] MDL 100907）后，以新皮层与小脑的比例获得了富含5-HT2A受体的新皮层区域的明显积累。 60-80分钟后的3.5-4.5。在新皮层区域，在40-60分钟内发生了短暂的平衡。注射酮色林后，新皮层中的放射性降低，但小脑中的放射性降低，这表明注射[11C] MDL 100907后的新皮层放射性代表与5-HT2A受体的特异性结合。