2-[(3-hydroxyphenyl)methyl]-1-methylpiperidine | 139158-22-8

• 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-hydroxyphenyl)methyl]-1-methylpiperidine
• 英文别名: N-methyl-2-(m-hydroxy-benzyl)piperidine；N-methyl-2-(3-hydroxybenzyl)piperidine；3-[(1-Methylpiperidin-2-yl)methyl]phenol
• CAS: 139158-22-8
• 化学式: C₁₃H₁₉NO
• 分子量: 205.3
• InChiKey: IFZRMDGYWUQECK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  23.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-[(3-hydroxyphenyl)methyl]-1-methylpiperidine 、 N,N-二乙基氯甲酰胺 在 吡啶 、 三乙胺 作用下， 以67%的产率得到2-[(3-diethylcarbamoyloxyphenyl)methyl]-1-methylpiperidine
  参考文献：
  名称：

  Synthesis and cholinesterase activity of phenylcarbamates related to Rivastigmine, a therapeutic agent for Alzheimer's disease

  摘要：

  In order to develop new cholinesterase agents effective against Alzheimer's disease (AD) we synthesized some phenylcarbamates structurally related to Rivastigmine and evaluated their in vitro and in vivo biological activity. Among the compounds which displayed the most significant in vitro activity, 1-[1-(3-dimethylcarbamoyloxyphenyl)ethyl]piperidine (31b), in addition to a simple and cheaper synthesis, showed lower toxicity and very similar therapeutic index in comparison with Rivastigmine. (C) 2002 Editions scientifiques et medicales Elsevier SAS. All rights reserved.

  DOI：

  10.1016/s0223-5234(01)01324-1
• 作为产物：
  描述：

  3-甲氧基氯苄 在 三溴化硼 、 sodium cyanoborohydride 、 magnesium 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 、 异丙醇 为溶剂， 反应 3.17h， 生成 2-[(3-hydroxyphenyl)methyl]-1-methylpiperidine
  参考文献：
  名称：

  Structure-activity studies of morphine fragments. II. Synthesis, opiate receptor binding, analgetic activity and conformational studies of 2-R-2(hydroxybenzyl)piperidines

  摘要：

  In this study, a series of 2-benzyl piperidines, that can be regarded as flexible fragments of fused ring opioids, have been synthesized and their pharmacological and conformational profiles determined. These combined studies reveal that, despite the weak activity of the only analog previously reported, modifications of it can lead to compounds with significant opioid receptor affinity and analgetic activity. Conformational studies of these compounds indicate that they can bind to these receptors in either an phenyl-axial and phenyl-equatorial conformer. Features such as the position of the phenolic OH group, the nature of the other 2-substituent and of the N-substituent appear to modulate receptor recognition and activation. However, the 2-benzyl piperidines do not appear to bind or act at the opioid receptors in the same conformation or orientation as their more rigid fused ring counterparts, the benzomorphans. In general, a change from p-OH to m-OH benzyl analogs reduces efficacy and its is possible that the m-OH analogs could be promising analgesics with low physical dependence liability.

  DOI：

  10.1016/0223-5234(91)90002-5

文献信息

• HETEROARYL COMPOUNDS, COMPOSITIONS THEREOF, AND METHODS OF TREATMENT THEREWITH
  申请人：Signal Pharmaceuticals LLC

  公开号：EP2078016A2

  公开（公告）日：2009-07-15
• [EN] HETEROARYL COMPOUNDS, COMPOSITIONS THEREOF, AND METHODS OF TREATMENT THEREWITH<br/>[FR] COMPOSÉS HÉTÉROARYLE, COMPOSITIONS CONTENANT CES COMPOSÉS ET PROCÉDÉS DE TRAITEMENT FAISANT APPEL À CES COMPOSÉS
  申请人：SIGNAL PHARM LLC

  公开号：WO2008051493A2

  公开（公告）日：2008-05-02

  [EN] Provided herein are Heteroaryl Compounds having the following structure: (I) wherein R¹, R², L, X, Y, Z, Q, A and B are as defined herein, compositions comprising an effective amount of a Heteroaryl Compound and methods for treating or preventing cancer, inflammatory conditions, immunological conditions, metabolic conditions and conditions treatable or preventable by inhibition of a kinase pathway comprising administering an effective amount of a Heteroaryl Compound to a patient in need thereof.
  [FR] L'invention concerne des composés hétéroaryle de formule (I). Dans cette formule, R¹, R², L, X, Y, Z, Q, A et B sont définis dans la description. L'invention concerne également des compositions comprenant une quantité efficace d'un composé hétéroaryle, et des procédés de traitement ou de prévention d'un cancer, de troubles inflammatoires, de troubles immunologiques, de troubles métaboliques et de troubles pouvant être traités ou prévenus par inhibition d'une voie kinase. Ces procédés consistent à administrer une quantité efficace d'un composé hétéroaryle à un patient qui en a besoin.
• Synthesis and cholinesterase activity of phenylcarbamates related to Rivastigmine, a therapeutic agent for Alzheimer's disease
  作者：C MUSTAZZA、A BORIONI、M GIUDICE、F GATTA、R FERRETTI、A MENEGUZ、M VOLPE、P LORENZINI

  DOI：10.1016/s0223-5234(01)01324-1

  日期：2002.2

  In order to develop new cholinesterase agents effective against Alzheimer's disease (AD) we synthesized some phenylcarbamates structurally related to Rivastigmine and evaluated their in vitro and in vivo biological activity. Among the compounds which displayed the most significant in vitro activity, 1-[1-(3-dimethylcarbamoyloxyphenyl)ethyl]piperidine (31b), in addition to a simple and cheaper synthesis, showed lower toxicity and very similar therapeutic index in comparison with Rivastigmine. (C) 2002 Editions scientifiques et medicales Elsevier SAS. All rights reserved.
• Structure-activity studies of morphine fragments. II. Synthesis, opiate receptor binding, analgetic activity and conformational studies of 2-R-2(hydroxybenzyl)piperidines
  作者：GH Loew、JA Lawson、L Toll、W Polgar、ET Uyeno

  DOI：10.1016/0223-5234(91)90002-5

  日期：1991.11

  In this study, a series of 2-benzyl piperidines, that can be regarded as flexible fragments of fused ring opioids, have been synthesized and their pharmacological and conformational profiles determined. These combined studies reveal that, despite the weak activity of the only analog previously reported, modifications of it can lead to compounds with significant opioid receptor affinity and analgetic activity. Conformational studies of these compounds indicate that they can bind to these receptors in either an phenyl-axial and phenyl-equatorial conformer. Features such as the position of the phenolic OH group, the nature of the other 2-substituent and of the N-substituent appear to modulate receptor recognition and activation. However, the 2-benzyl piperidines do not appear to bind or act at the opioid receptors in the same conformation or orientation as their more rigid fused ring counterparts, the benzomorphans. In general, a change from p-OH to m-OH benzyl analogs reduces efficacy and its is possible that the m-OH analogs could be promising analgesics with low physical dependence liability.