MHMZ | 1018473-90-9

• 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: MHMZ
• 英文别名: (3-(2-fluoroethoxy)-2-methoxyphenyl)-(1-(2-p-fluorophenylethyl)-piperidin-4-yl)-methanol；(1-(4-Fluorophenethyl)piperidin-4-yl)(3-(2-fluoroethoxy)-2-methoxyphenyl)methanol；[3-(2-fluoroethoxy)-2-methoxyphenyl]-[1-[2-(4-fluorophenyl)ethyl]piperidin-4-yl]methanol
• CAS: 1018473-90-9
• 化学式: C₂₃H₂₉F₂NO₃
• 分子量: 405.485
• InChiKey: QCFZUTYIUYQTPW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  29
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  41.9
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  MA-1 在 sodium tetrahydroborate 、 ammonium hydroxide 作用下， 以 甲醇 为溶剂， 生成 MHMZ
  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

• Total synthesis and evaluation of [18F]MHMZ
  作者：Matthias M. Herth、Fabian Debus、Markus Piel、Mikael Palner、Gitte M. Knudsen、Hartmut Lüddens、Frank Rösch

  DOI：10.1016/j.bmcl.2007.12.054

  日期：2008.2

  Radiochemical labeling of MDL 105725 using the secondary labeling precursor 2-[F-18] fluoroethyltosylate ([F-18] FETos) was carried out in yields of similar to 90% synthesizing [F-18] MHMZ in a speci. c activity of similar to 50 MBq/ nmol with a starting activity of similar to 3 GBq. Overall radiochemical yield including [F-18] FETos synthon synthesis, [F-18] fluoroalkylation and preparing the injectable [ 18 F] MHMZ solution was 42% within a synthesis time of similar to 100 min. The novel compound showed excellent speci. c binding to the 5-HT2A receptor (K-i = 9.0 nM) in vitro and promising in vivo characteristics. (C) 2007 Elsevier Ltd. All rights reserved.