(R,S)-(5-methoxy-2,3-dihydro-1,4-benzodioxin-2-yl)methanol | 150711-00-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并二恶烷
• 英文名称: (R,S)-(5-methoxy-2,3-dihydro-1,4-benzodioxin-2-yl)methanol
• 英文别名: (5-Methoxy-2,3-dihydro-1,4-benzodioxin-2-yl)methanol
• CAS: 150711-00-5
• 化学式: C₁₀H₁₂O₄
• 分子量: 196.203
• InChiKey: NBVYKJUTDVMELA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  47.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (R,S)-(5-methoxy-2,3-dihydro-1,4-benzodioxin-2-yl)methanol 在 吡啶 、 potassium carbonate 作用下， 以 乙腈 为溶剂， 反应 72.0h， 生成 (5-Methoxy-2,3-dihydro-benzo[1,4]dioxin-2-ylmethyl)-(1-pyrimidin-2-yl-piperidin-4-ylmethyl)-amine
  参考文献：
  名称：

  N-Substituted (2,3-Dihydro-1,4-benzodioxin-2-yl)methylamine Derivatives as D₂ Antagonists/5-HT_1A Partial Agonists with Potential as Atypical Antipsychotic Agents

  摘要：

  A series of N-substituted 1-(2,3-dihydro-1,4-benzodioxin-2-yl)methylamine derivatives with D-2 antagonist/5-HT1A partial agonist activity has been prepared as potential atypical antipsychotic agents. Optimization of in vitro receptor binding activity and in vivo activity in rodent models of psychosis has led to compound 24, which showed good affinities for human D-2, D-3, and 5-HT1A receptors but significantly less affinity for human alpha(1) adrenoceptors and rat H-1 and muscarinic receptors. In rodents, 24 showed functional D-2-like antagonism and 5-HT1A partial agonism. After oral dosing, 24 showed good activity in rodent antipsychotic tests and very little potential to cause extrapyramidal side effects (EPS), as measured by its ability to induce catalepsy in rats only at very high doses. In the light of this promising profile of activity, 24 has been selected for clinical investigation as a novel antipsychotic agent with a predicted low propensity to cause EPS.

  DOI：

  10.1021/jm9910122
• 作为产物：
  描述：

  5-methoxy-2,3-dihydro-1,4-benzodioxin-2-carboxamide 在 盐酸 、 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 反应 18.0h， 生成 (R,S)-(5-methoxy-2,3-dihydro-1,4-benzodioxin-2-yl)methanol
  参考文献：
  名称：

  N-Substituted (2,3-Dihydro-1,4-benzodioxin-2-yl)methylamine Derivatives as D₂ Antagonists/5-HT_1A Partial Agonists with Potential as Atypical Antipsychotic Agents

  摘要：

  A series of N-substituted 1-(2,3-dihydro-1,4-benzodioxin-2-yl)methylamine derivatives with D-2 antagonist/5-HT1A partial agonist activity has been prepared as potential atypical antipsychotic agents. Optimization of in vitro receptor binding activity and in vivo activity in rodent models of psychosis has led to compound 24, which showed good affinities for human D-2, D-3, and 5-HT1A receptors but significantly less affinity for human alpha(1) adrenoceptors and rat H-1 and muscarinic receptors. In rodents, 24 showed functional D-2-like antagonism and 5-HT1A partial agonism. After oral dosing, 24 showed good activity in rodent antipsychotic tests and very little potential to cause extrapyramidal side effects (EPS), as measured by its ability to induce catalepsy in rats only at very high doses. In the light of this promising profile of activity, 24 has been selected for clinical investigation as a novel antipsychotic agent with a predicted low propensity to cause EPS.

  DOI：

  10.1021/jm9910122

文献信息

• BENZODIOXANE DERIVATIVE
  申请人：Chugai Seiyaku Kabushiki Kaisha

  公开号：EP0565732B1

  公开（公告）日：1998-01-14
• US5480905A
  申请人：——

  公开号：US5480905A

  公开（公告）日：1996-01-02