[4-(Pyrimidin-2-ylamino)-cyclohexyl]-acetic acid ethyl ester | 189153-07-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: [4-(Pyrimidin-2-ylamino)-cyclohexyl]-acetic acid ethyl ester
• CAS: 189153-07-9
• 化学式: C₁₄H₂₁N₃O₂
• 分子量: 263.34
• InChiKey: CROFOHPQKDBQHS-HAQNSBGRSA-N

物化性质

• 沸点：
  402.9±37.0 °C(Predicted)
• 密度：
  1.135±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  19.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  64.11
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  [4-(Pyrimidin-2-ylamino)-cyclohexyl]-acetic acid ethyl ester 在 lithium aluminium tetrahydride 、 三苯基膦树脂 、 四溴化碳 、 potassium carbonate 作用下， 以 四氢呋喃 、 二氯甲烷 、 乙腈 为溶剂， 反应 19.75h， 生成 Pyrimidin-2-yl-{4-[2-(2,3,5,6-tetrahydro-[1,2']bipyrazinyl-4-yl)-ethyl]-cyclohexyl}-amine
  参考文献：
  名称：

  Aminopyrimidines with High Affinity for Both Serotonin and Dopamine Receptors

  摘要：

  A series of {4-[2-(4-arylpiperazin-1-yl)alkyl]cyclohexyl}pyrimidin-2-ylamines was prepared and found to have receptor binding affinity for D2 and D3 dopamine (DA) receptors and serotonin 5-HT1A receptors. The structural contributions to D2/D3 and 5-HT1A receptor binding of the aminopyrimidine, cycloalkyl, and phenylpiperazine portions of the molecule were examined. From these studies compounds 14, 39, 42, 43, having potent affinity for both DA D2 and 5-HT1A receptors, were evaluated for intrinsic activity at these receptors, in vitro and in vivo. Compound 14 (PD 158771) had a profile indicative of partial agonist activity at both D2 and 5-HT1A receptors causing partially decreased synthesis of the neurotransmitters DA and 5-HT and their metabolites. This compound has a profile in behavioral tests that is predictive of antipsychotic activity, suggesting that mixed, partial agonists such as 14 may have utility as antipsychotic agents with increased efficacy and decreased side effects.

  DOI：

  10.1021/jm9707378
• 作为产物：
  描述：

  trans-(4-amino-cyclohexyl)-acetic acid 在 盐酸 、 三乙胺 作用下， 以 乙醇 为溶剂， 反应 22.0h， 生成 [4-(Pyrimidin-2-ylamino)-cyclohexyl]-acetic acid ethyl ester
  参考文献：
  名称：

  Aminopyrimidines with High Affinity for Both Serotonin and Dopamine Receptors

  摘要：

  A series of {4-[2-(4-arylpiperazin-1-yl)alkyl]cyclohexyl}pyrimidin-2-ylamines was prepared and found to have receptor binding affinity for D2 and D3 dopamine (DA) receptors and serotonin 5-HT1A receptors. The structural contributions to D2/D3 and 5-HT1A receptor binding of the aminopyrimidine, cycloalkyl, and phenylpiperazine portions of the molecule were examined. From these studies compounds 14, 39, 42, 43, having potent affinity for both DA D2 and 5-HT1A receptors, were evaluated for intrinsic activity at these receptors, in vitro and in vivo. Compound 14 (PD 158771) had a profile indicative of partial agonist activity at both D2 and 5-HT1A receptors causing partially decreased synthesis of the neurotransmitters DA and 5-HT and their metabolites. This compound has a profile in behavioral tests that is predictive of antipsychotic activity, suggesting that mixed, partial agonists such as 14 may have utility as antipsychotic agents with increased efficacy and decreased side effects.

  DOI：

  10.1021/jm9707378

文献信息

• Substituted cyclohexylamines as central nervous systems agents
  申请人：Warner-Lambert Company

  公开号：US05977110A1

  公开（公告）日：1999-11-02

  Substituted cyclohexylamines and derivatives thereof are described, as well as methods for the preparation and pharmaceutical composition of same, which are useful as central nervous system agents and are particularly useful as dopaminergic, serotonergic, antipsychotic, and anxiolytic agents.

  本文描述了取代的环己胺及其衍生物，以及制备方法和制药组合物，其作为中枢神经系统药物非常有用，特别是作为多巴胺能、血清素能、抗精神病和抗焦虑药物。
• US5977110A
  申请人：——

  公开号：US5977110A

  公开（公告）日：1999-11-02