3-(3-甲氧基-5-甲基-1,2-恶唑-4-基)丙醛 | 154229-60-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 3-(3-甲氧基-5-甲基-1,2-恶唑-4-基)丙醛
• 英文名称: 3-(3-methoxy-5-methyl-4-isoxazolyl)propionaldehyde
• 英文别名: 3-(3-methoxy-5-methyl-1,2-oxazol-4-yl)propanal
• CAS: 154229-60-4
• 化学式: C₈H₁₁NO₃
• 分子量: 169.18
• InChiKey: JAEJHAKISZEODP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  12
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  52.3
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-(3-甲氧基-5-甲基-1,2-恶唑-4-基)丙醛 在 盐酸 作用下， 以 甲醇 、 水 为溶剂， 反应 54.0h， 生成 (RS)-2-amino-4-(3-hydroxy-5-methyl-4-isoxazolyl)butyric acid
  参考文献：
  名称：

  Design, synthesis and pharmacology of model compounds for indirect elucidation of the topography of AMPA receptor sites

  摘要：

  Based on structure-activity studies on excitatory amino acids with specific agonist effect at (RS)-2-amino-3-(3-hydroxy-5-methyl-4-isoxazolyl)propionic acid (AMPA) receptors we have earlier proposed a simple model of the AMPA receptor pharamacophore. In order to judge the capacity of this empirical model we have now synthesized and tested 3 model compounds derived from the AMPA receptor agonists, AMPA and (RS)-3-hydroxy-4,5,6,7-tetrahydroisoxazolo[5,4-c]pyridine-7-carboxylic acid (7-HCPA). These model compounds, (RS)-2-amino-3-(5-ethyl-3-hydroxy-4-isoxazolyl)propionic acid (Et-AMPA), (RS)-2-amino-4-(3-hydroxy-5-methyl-4-isoxazolyl)butyric acid (Homo-AMPA) and (RS)-3-hydroxy-5,6,7,8-tetrahydro-4H-isoxazolo[5,4-c]azepine-8-carboxylic acid (Homo-7-HCPA) were tested electrophysiologically and in receptor binding assays. Et-AMPA was slightly more potent than AMPA as an AMPA agonist (EC50 = 2.3 muM compared to 3.5 muM for AMPA) and as a specific inhibitor of [H-3]AMPA binding (IC50 = 0.030 muM compared with 0.040 muM for AMPA), whereas Homo-AMPA was essentially inactive. Homo-7-HPCA was much weaker than 7-HPCA. These data support the view that the AMPA recognition site(s) comprise a confined region, which tightly binds the charged structure-elements of agonists molecules, and a cavity capable of accommodating bulky lipophilic groups in such compounds.

  DOI：

  10.1016/0223-5234(93)90114-t
• 作为产物：
  描述：

  ethyl 3-(3-methoxy-5-methyl-4-isoxazolyl)propionate 在 二异丁基氢化铝 作用下， 以 正己烷 、 甲苯 为溶剂， 反应 0.1h， 以88%的产率得到3-(3-甲氧基-5-甲基-1,2-恶唑-4-基)丙醛
  参考文献：
  名称：

  Design, synthesis and pharmacology of model compounds for indirect elucidation of the topography of AMPA receptor sites

  摘要：

  Based on structure-activity studies on excitatory amino acids with specific agonist effect at (RS)-2-amino-3-(3-hydroxy-5-methyl-4-isoxazolyl)propionic acid (AMPA) receptors we have earlier proposed a simple model of the AMPA receptor pharamacophore. In order to judge the capacity of this empirical model we have now synthesized and tested 3 model compounds derived from the AMPA receptor agonists, AMPA and (RS)-3-hydroxy-4,5,6,7-tetrahydroisoxazolo[5,4-c]pyridine-7-carboxylic acid (7-HCPA). These model compounds, (RS)-2-amino-3-(5-ethyl-3-hydroxy-4-isoxazolyl)propionic acid (Et-AMPA), (RS)-2-amino-4-(3-hydroxy-5-methyl-4-isoxazolyl)butyric acid (Homo-AMPA) and (RS)-3-hydroxy-5,6,7,8-tetrahydro-4H-isoxazolo[5,4-c]azepine-8-carboxylic acid (Homo-7-HCPA) were tested electrophysiologically and in receptor binding assays. Et-AMPA was slightly more potent than AMPA as an AMPA agonist (EC50 = 2.3 muM compared to 3.5 muM for AMPA) and as a specific inhibitor of [H-3]AMPA binding (IC50 = 0.030 muM compared with 0.040 muM for AMPA), whereas Homo-AMPA was essentially inactive. Homo-7-HPCA was much weaker than 7-HPCA. These data support the view that the AMPA recognition site(s) comprise a confined region, which tightly binds the charged structure-elements of agonists molecules, and a cavity capable of accommodating bulky lipophilic groups in such compounds.

  DOI：

  10.1016/0223-5234(93)90114-t

文献信息

• Design, synthesis and pharmacology of model compounds for indirect elucidation of the topography of AMPA receptor sites
  作者：U Madsen、B Frølund、TM Lund、B Ebert、P Krogsgaard-Larsen

  DOI：10.1016/0223-5234(93)90114-t

  日期：1993.1

  Based on structure-activity studies on excitatory amino acids with specific agonist effect at (RS)-2-amino-3-(3-hydroxy-5-methyl-4-isoxazolyl)propionic acid (AMPA) receptors we have earlier proposed a simple model of the AMPA receptor pharamacophore. In order to judge the capacity of this empirical model we have now synthesized and tested 3 model compounds derived from the AMPA receptor agonists, AMPA and (RS)-3-hydroxy-4,5,6,7-tetrahydroisoxazolo[5,4-c]pyridine-7-carboxylic acid (7-HCPA). These model compounds, (RS)-2-amino-3-(5-ethyl-3-hydroxy-4-isoxazolyl)propionic acid (Et-AMPA), (RS)-2-amino-4-(3-hydroxy-5-methyl-4-isoxazolyl)butyric acid (Homo-AMPA) and (RS)-3-hydroxy-5,6,7,8-tetrahydro-4H-isoxazolo[5,4-c]azepine-8-carboxylic acid (Homo-7-HCPA) were tested electrophysiologically and in receptor binding assays. Et-AMPA was slightly more potent than AMPA as an AMPA agonist (EC50 = 2.3 muM compared to 3.5 muM for AMPA) and as a specific inhibitor of [H-3]AMPA binding (IC50 = 0.030 muM compared with 0.040 muM for AMPA), whereas Homo-AMPA was essentially inactive. Homo-7-HPCA was much weaker than 7-HPCA. These data support the view that the AMPA recognition site(s) comprise a confined region, which tightly binds the charged structure-elements of agonists molecules, and a cavity capable of accommodating bulky lipophilic groups in such compounds.