2-{4-[2-(2-吡啶基氨基)乙基]-1-哌嗪基}苯酚 | 146714-76-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪烷类
• 中文名称: 2-{4-[2-(2-吡啶基氨基)乙基]-1-哌嗪基}苯酚
• 英文名称: 2-(2-(1-(4-(2-hydroxyphenyl)piperazinyl)ethyl)amino)pyridine
• 英文别名: N-(2-(4-(2-hydroxyphenyl)piperazin-1-yl)ethyl)-N-(2-pyridinyl)amine；desmethyl-WAY-100634；N-(2-(4-(2-hydroxyphenyl)piperazin-1-yl)ethyl)pyridin-2-amine；O-desmethyl WAY-100634；2-(4-(2-(Pyridin-2-ylamino)ethyl)piperazin-1-yl)phenol；2-[4-[2-(pyridin-2-ylamino)ethyl]piperazin-1-yl]phenol
• CAS: 146714-76-3
• 化学式: C₁₇H₂₂N₄O
• 分子量: 298.388
• InChiKey: WOGPQIKDHNDUNU-UHFFFAOYSA-N

物化性质

• 沸点：
  506.3±50.0 °C(Predicted)
• 密度：
  1.213±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  51.6
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  [carbonyl-11C]cyclohexanecarbonyl chloride 、 2-{4-[2-(2-吡啶基氨基)乙基]-1-哌嗪基}苯酚 在 N,N-二异丙基乙胺 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 0.08h， 生成 [carbonyl-11C]N-(2-(4-(2-hydroxyphenyl)piperazin-1-yl)ethyl)-N-(2-pyridinyl)-cyclohexanecarboxamide
  参考文献：
  名称：

  Maiti, D. K.; Chakraborty, P. K.; Chugani, D. C., Journal of labelled compounds and radiopharmaceuticals, 2003, vol. 46, p. S233 - S233

  摘要：

  DOI：
• 作为产物：
  描述：

  2-氯-N-吡啶-2-基乙酰胺 在 dimethyl sulfide borane 、 potassium carbonate 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 生成 2-{4-[2-(2-吡啶基氨基)乙基]-1-哌嗪基}苯酚
  参考文献：
  名称：

  N- {2- [4-（2-甲氧基苯基）哌嗪-1-基]乙基} -N-（吡啶-2-基）环己烷甲酰胺的桥头碘化类似物的设计，合成，放射标记以及体外和体内评价（WAY-100635）作为5-HT 1A受体的潜在SPECT配体

  摘要：

  在这里，我们描述与1（WAY-100635）相关的5-HT 1A受体配体的设计，合成和药理学特征。在环己基部分1和其O形脱甲基类似物3是由桥头碘化桥接稠环替代：金刚烷基，cubyl，双环[2.2.2]辛基，或二环[2.2.1]庚基。在体外，所有类似物均对5-HT 1A受体表现出（亚）纳摩尔亲和力。化合物6b和7b似乎对该受体具有比其他相关受体更高的选择性，并且可以很容易地用放射性碘123碘化。在人肝细胞中，[ 123 I] 6b表现出较低的酰胺水解倾向和稳定的碳碘键。[ 123 I] 6b和[ 123 I] 7b在大鼠中的生物分布表明，碳碘键在体内也很稳定。不幸的是，两种放射性配体的脑摄取和特异性均显着低于母体分子1。总之，设计的示踪剂不适用于SPECT成像。

  DOI：

  10.1021/jm1009956

文献信息

• Piperazine derivatives
  申请人：JOHN WYETH & BROTHER LIMITED

  公开号：EP0512755A2

  公开（公告）日：1992-11-11

  Piperazine derivatives of formula I and their pharmaceutically acceptable acid addition salts are 5-HTIA binding agents, particularly 5-HTIA antagonists and may be used, for example, as anxiolytics. In the formula A is C2-4 alkylene chain optionally substituted by lower alkyl, Z is oxygen or sulphur, R is hydrogen or lower alkyl, R1 is a mono or bicyclic aryl or heteroaryl radical, R2 is a mono or bicyclic heteroaryl radical and R3 is hydrogen or a specified radical such as lower alkyl, cycloalkyl, aryl, heteroaryl or optionally substituted amino.

  式 I 的哌嗪衍生物 及其药学上可接受的酸加成盐是 5-HTIA 结合剂，特别是 5-HTIA 拮抗剂，可用作抗焦虑药等。在式中，A 是任选被低级烷基取代的 C2-4 烷链，Z 是氧或硫，R 是氢或低级烷基，R1 是单环或双环芳基或杂芳基，R2 是单环或双环杂芳基，R3 是氢或特定的基，如低级烷基、环烷基、芳基、杂芳基或任选取代的氨基。
• Pike, Victor W.; McCarron, Julie A.; Hume, Susan P., Medicinal Chemistry Research, 1995, vol. 5, # 2/3, p. 208 - 227
  作者：Pike, Victor W.、McCarron, Julie A.、Hume, Susan P.、Ashworth, Sharon、Opacka-Juffry, Jolanta、et al.

  DOI：——

  日期：——
• Design, synthesis and in vitro evaluation of bridgehead fluoromethyl analogs of N-{2-[4-(2-methoxyphenyl)piperazin-1-yl]ethyl}-N-(pyridin-2-yl)cyclohexanecarboxamide (WAY-100635) for the 5-HT1A receptor
  作者：Rana Al Hussainy、Joost Verbeek、Dion van der Born、Jan Booij、J(Koos) D.M. Herscheid

  DOI：10.1016/j.ejmech.2011.06.023

  日期：2011.12

  Fluorinated analogs that are related to the 5-hydroxytryptamine (5-HT1A) antagonist, N-2-[4-(2-methoxyphenyl)piperazin-1-yl]ethyl}-N-(pyridin-2-yl)cyclohexanecarboxamide (WAY-100635), have been synthesized and their binding affinity for the 5-HT1A receptor and other neurotransmitter receptors (adrenoceptors, sigma receptors, and dopamine receptors), and serotonin transporters was examined in vitro. These ligands were designed to provide a possible potential positron emission tomography (PET) ligand with high metabolic stability. To this end, the cyclohexyl moiety in WAY-100635 and in O-desmethyl WAY-100635 was replaced by a bridge-fused ring (BFR) such as adamantyl, cubyl, bicyclo[2.2.2] octyl and bicyclo[2.2.1]heptyl to reduce the metabolic rate of the amide bond hydrolysis, while a fluoromethyl group was introduced on the other bridgehead of the BFR to prevent defluorination by HE elimination. All synthesized analogs displayed high affinity in the (sub)nanomolar range for the 5-HT1A receptor, comparable to WAY-100635. In addition, 6b, 6c and 6d were reasonably selective to the 5-HT1A receptor over the above mentioned receptors. In human hepatocytes, 6b showed a suitable metabolic stability.In conclusion, the obtained data provides a promising starting point for the synthesis of the corresponding F-18-labeled PET analogs. (C) 2011 Elsevier Masson SAS. All rights reserved.
• Pike, V.W.; McCarron, J.A.; Lundkvist, C., Journal of labelled compounds and radiopharmaceuticals, 1997, vol. 40, p. 568 - 570
  作者：Pike, V.W.、McCarron, J.A.、Lundkvist, C.、Halldin, C.、Hume, S.P.、et al.

  DOI：——

  日期：——
• METHOD FOR DETECTING ALZHEIMER"S DISEASE AND OTHER FORMS OF DEMENTIA, AND MEASURING THEIR PROGRESSION
  申请人：The Regents of the University of California System

  公开号：EP1768705A2

  公开（公告）日：2007-04-04