2-hydroxymethyl-3-dimethylaminocarbonyloxypyridine | 403729-90-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 2-hydroxymethyl-3-dimethylaminocarbonyloxypyridine
• 英文别名: [2-(hydroxymethyl)pyridin-3-yl] N,N-dimethylcarbamate
• CAS: 403729-90-8
• 化学式: C₉H₁₂N₂O₃
• 分子量: 196.206
• InChiKey: IEDDELXMBQXJGD-UHFFFAOYSA-N

物化性质

• 沸点：
  338.9±42.0 °C(Predicted)
• 密度：
  1.242±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  62.7
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-hydroxymethyl-3-dimethylaminocarbonyloxypyridine 以 吡啶 、 二氯甲烷 为溶剂， 反应 0.5h， 生成
  参考文献：
  名称：

  Facile synthesis and PET imaging of a novel potential heart acetylcholinesterase tracer N-[11C]methyl-3-[[(dimethylamino)carbonyl]oxy]-2-(2′,2′-diphenylpropionoxymethyl)pyridinium

  摘要：

  A new AChE tracer N-[C-11]methyl-3-[[(dimethylamino)carbonyl]oxy]-2-(2 ',2 '-diphenylpropionoxymethyl)pyridinium ([C-11]MDDP, [C-11]1) has been synthesized in 40-65% radiochemical yield. Initial PET dynamic studies of [C-11] MDDP in rat heart showed rapid heart uptake and blood pool clearance to give high-quality heart images. Blocking studies of [I C]MDDP with pretreatment drug neostigmine in rats found only minor reductions in rat heart [C-11]MDDP retention. The results suggest that [C-11]MDDP delineates the heart very clearly, and the uptakes of [C-11]MDDP in rat heart might be related to non-specific binding. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.07.034
• 作为产物：
  描述：

  3-羟基-2-羟甲基吡啶盐酸盐 、 二甲氨基甲酰氯 以31%的产率得到2-hydroxymethyl-3-dimethylaminocarbonyloxypyridine
  参考文献：
  名称：

  Facile synthesis and PET imaging of a novel potential heart acetylcholinesterase tracer N-[11C]methyl-3-[[(dimethylamino)carbonyl]oxy]-2-(2′,2′-diphenylpropionoxymethyl)pyridinium

  摘要：

  A new AChE tracer N-[C-11]methyl-3-[[(dimethylamino)carbonyl]oxy]-2-(2 ',2 '-diphenylpropionoxymethyl)pyridinium ([C-11]MDDP, [C-11]1) has been synthesized in 40-65% radiochemical yield. Initial PET dynamic studies of [C-11] MDDP in rat heart showed rapid heart uptake and blood pool clearance to give high-quality heart images. Blocking studies of [I C]MDDP with pretreatment drug neostigmine in rats found only minor reductions in rat heart [C-11]MDDP retention. The results suggest that [C-11]MDDP delineates the heart very clearly, and the uptakes of [C-11]MDDP in rat heart might be related to non-specific binding. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.07.034

文献信息

• Pyridophens:  Binary Pyridostigmine−Aprophen Prodrugs with Differential Inhibition of Acetylcholinesterase, Butyrylcholinesterase, and Muscarinic Receptors
  作者：Haim Leader、Alan David Wolfe、Peter K. Chiang、Richard K. Gordon

  DOI：10.1021/jm010196t

  日期：2002.2.1

  A series of ''binary prodrugs'' called carbaphens,(1) carbamylated derivatives on one or both of the aromatic rings of the muscarinic receptor antagonist aprophen [(N,N-diethylaniino)ethyl 2,2-diphenylpropionatel, were synthesized to develop binary prophylactic agents against organophosphorus intoxication. As a group, the carbaphens retained the muscarinic receptor antagonist properties of aprophen but also preferentially inhibited butyrylcholinesterase (BChE) in contrast to acetylholinesterase (AChE). Therefore, a new series of compounds named pyridophens were designed and synthesized to achieve binary prodrugs to preferentially inhibit AChE over BChE, while still retaining the muscarinic receptor antagonism of aprophen. The pyridophens consist of the basic pyridostigmine skeleton combined with the 2,2-diplienylpropionate portion of aprophen by replacement of the diethylamino group. Three compounds, 9 (a tertiary pyridine), 10 (a quaternary pyridine), and 12 (a tertiary tetrahydropyridine), were found to be effective inhibitors of both BChE and AChE. However, 10, N-methyl-3-[[(dimethylamino)carbonylloxyl-2-(2'2'-diphenylpropionoxy-methyl)pyridinium iodide, inhibited AChE selectively over BChE, with a bimolecular rate constant similar to pyridostigmine. In contrast to their potent cholinesterase inhibitory activity, all of the pyridophen analogues were less potent antagonists of the muscarinic receptor than aprophen.
• Facile synthesis and PET imaging of a novel potential heart acetylcholinesterase tracer N-[11C]methyl-3-[[(dimethylamino)carbonyl]oxy]-2-(2′,2′-diphenylpropionoxymethyl)pyridinium
  作者：Ji-Quan Wang、Michael A. Miller、Bruce H. Mock、John C. Lopshire、William J. Groh、Douglas P. Zipes、Gary D. Hutchins、Qi-Huang Zheng

  DOI：10.1016/j.bmcl.2005.07.034

  日期：2005.10

  A new AChE tracer N-[C-11]methyl-3-[[(dimethylamino)carbonyl]oxy]-2-(2 ',2 '-diphenylpropionoxymethyl)pyridinium ([C-11]MDDP, [C-11]1) has been synthesized in 40-65% radiochemical yield. Initial PET dynamic studies of [C-11] MDDP in rat heart showed rapid heart uptake and blood pool clearance to give high-quality heart images. Blocking studies of [I C]MDDP with pretreatment drug neostigmine in rats found only minor reductions in rat heart [C-11]MDDP retention. The results suggest that [C-11]MDDP delineates the heart very clearly, and the uptakes of [C-11]MDDP in rat heart might be related to non-specific binding. (c) 2005 Elsevier Ltd. All rights reserved.