1-乙基-4-羟基-4-(3-甲氧基苯基)哌啶 | 102573-71-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 中文名称: 1-乙基-4-羟基-4-(3-甲氧基苯基)哌啶
• 英文名称: 1-ethyl-4-hydroxy-4-(3-methoxyphenyl)piperidine
• 英文别名: N-ethyl-4-hydroxy-4-(3-methoxyphenyl)piperidine；1-ethyl-4-(3-methoxyphenyl)piperidin-4-ol
• CAS: 102573-71-7
• 化学式: C₁₄H₂₁NO₂
• 分子量: 235.326
• InChiKey: JEILUSZIWAFOGL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  32.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-乙基-4-羟基-4-(3-甲氧基苯基)哌啶 在 正丁基锂 、 磷酸 作用下， 反应 3.17h， 生成 4-(4-Chloro-butyl)-1-ethyl-4-(3-methoxy-phenyl)-1,2,3,4-tetrahydro-pyridine
  参考文献：
  名称：

  Characterization of the neurotoxic potential of m-methoxy-MPTP and the use of its N-ethyl analog as a means of avoiding exposure to a possible Parkinson-causing agent

  摘要：

  1-Methyl-4-(3-methoxyphenyl)-1,2,3,6-tetrahydropyridine (2) produced persistent depletion of striatal dopamine in mice after four daily injections, although it was less potent than 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine (MPTP). MPTP has been implicated as a cause of Parkinsonism in drug abusers who inadvertently self-administered it and in industrial chemists who were exposed to it. Our results suggest that the m-methoxy compound has the same neurotoxic potential to cause destruction of nigrostriatal dopamine neurons that would lead to Parkinsonian symptoms in humans. In contrast, 1-ethyl-4-(3-methoxyphenyl)-1,2,3,6-tetrahydropyridine (11) had no effects on striatal dopamine in mice, even at doses 8 times those of MPTP. A method of preparing 11 and using it as an intermediate in the synthesis of potential analgesic drugs, thus avoiding a potentially neurotoxic intermediate, is described.

  DOI：

  10.1021/jm00158a033
• 作为产物：
  描述：

  N-乙基-4-哌啶酮 、 间溴苯甲醚 在 正丁基锂 作用下， 生成 1-乙基-4-羟基-4-(3-甲氧基苯基)哌啶
  参考文献：
  名称：

  Characterization of the neurotoxic potential of m-methoxy-MPTP and the use of its N-ethyl analog as a means of avoiding exposure to a possible Parkinson-causing agent

  摘要：

  1-Methyl-4-(3-methoxyphenyl)-1,2,3,6-tetrahydropyridine (2) produced persistent depletion of striatal dopamine in mice after four daily injections, although it was less potent than 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine (MPTP). MPTP has been implicated as a cause of Parkinsonism in drug abusers who inadvertently self-administered it and in industrial chemists who were exposed to it. Our results suggest that the m-methoxy compound has the same neurotoxic potential to cause destruction of nigrostriatal dopamine neurons that would lead to Parkinsonian symptoms in humans. In contrast, 1-ethyl-4-(3-methoxyphenyl)-1,2,3,6-tetrahydropyridine (11) had no effects on striatal dopamine in mice, even at doses 8 times those of MPTP. A method of preparing 11 and using it as an intermediate in the synthesis of potential analgesic drugs, thus avoiding a potentially neurotoxic intermediate, is described.

  DOI：

  10.1021/jm00158a033

文献信息

• Treatment of pruritus
  申请人：Pfizer Inc.

  公开号：US05972962A1

  公开（公告）日：1999-10-26

  The use of certain known 1,3,4 trisubstituted 4-aryl-piperidines for the treatment of pruritus in humans and animals is disclosed.

  揭示了利用某些已知的1,3,4-三取代基的4-芳基哌啶类化合物用于治疗人类和动物的瘙痒症状。
• IMIDAZO[1,2-A]PYRIDINE DERIVATIVES AND THEIR USE AS POSITIVE ALLOSTERIC MODULATORS OF MGLUR2 RECEPTORS
  申请人：Trabanco-Suarez Andres Avelino

  公开号：US20110009441A1

  公开（公告）日：2011-01-13

  The present invention relates to novel compounds, in particular novel imidazo[1,2-a]piridine derivatives according to Formula (I). The compounds according to the invention are positive allosteric modulators of metabotropic receptors-sub-type 2 (‘mGluR2’) which are useful for the treatment or prevention of neurological and psychiatric disorders associated with glutamate dysfunction and diseases in which the mGluR2 subtype of metabotropic receptors is involved. In particular, such diseases are central nervous system disorders selected from the group of anxiety, schizophrenia, migraine, depression, and epilepsy. The invention is also directed to pharmaceutical compositions and processes to prepare such compounds and compositions, as well as to the use of such compounds for the prevention and treatment of such diseases in which mGluR2 is involved.

  本发明涉及新型化合物，特别是公式（I）中的新型咪唑并[1,2-a]吡啶衍生物。本发明的化合物是代谢型受体亚型2（“mGluR2”）的阳性变构调节剂，可用于治疗或预防与谷氨酸功能障碍有关的神经和精神障碍以及涉及代谢型受体亚型mGluR2的疾病。特别是，这些疾病是来自焦虑、精神分裂症、偏头痛、抑郁症和癫痫等中枢神经系统疾病的群体。本发明还涉及制备这些化合物和组合物的制药组合物和制备过程，以及将这些化合物用于预防和治疗涉及mGluR2的这些疾病的用途。
• ZIMMERMAN D. M.; CANTRELL B. E.; REEL J. K.; HEMRICK-LUECKE S. K.; FULLER+, J. MED. CHEM., 29,(1986) N 8, 1517-1520
  作者：ZIMMERMAN D. M.、 CANTRELL B. E.、 REEL J. K.、 HEMRICK-LUECKE S. K.、 FULLER+

  DOI：——

  日期：——
• US5972962A
  申请人：——

  公开号：US5972962A

  公开（公告）日：1999-10-26
• US8785486B2
  申请人：——

  公开号：US8785486B2

  公开（公告）日：2014-07-22