(RS)-methyl 3-hydroxy-4,5,6,7-tetrahydroisoxazolo<5,4-c>pyridine-7-carboxylate hydrobromide | 89017-62-9

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (RS)-methyl 3-hydroxy-4,5,6,7-tetrahydroisoxazolo<5,4-c>pyridine-7-carboxylate hydrobromide
• CAS: 89017-62-9
• 化学式: BrH*C₈H₁₀N₂O₄
• 分子量: 279.09
• InChiKey: KFFSRUHGJNQCAE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.32
• 重原子数：
  15.0
• 可旋转键数：
  1.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  84.59
• 氢给体数：
  2.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  (RS)-methyl 3-hydroxy-4,5,6,7-tetrahydroisoxazolo<5,4-c>pyridine-7-carboxylate hydrobromide 在 Amberlite IRA-400 作用下， 生成 3-羟基-4,5,6,7-四氢[1,2]恶唑并[5,4-c]吡啶-7-羧酸
  参考文献：
  名称：

  Ibotenic acid analogs. Synthesis and biological and in vitro activity of conformationally restricted agonists at central excitatory amino acid receptors

  摘要：

  A number of analogues of ibotenic acid [(RS)-3-hydroxy-5- isoxazoleglycine ] were synthesized; they were tested as excitants on neurons in the cat spinal cord, by using microelectrophoretic techniques, and as inhibitors of the binding of kainic acid (KA) in vitro, by using synaptic membranes prepared from rat brains. The excitatory effects of the 3- isoxazolol amino acids (RS)-3-hydroxy-4,5,6,7-tetrahydroisoxazolo[5, 4-c]pyridine-7-carboxylic acid (4, 7- HPCA ), (RS)-alpha-amino-3-hydroxy-5,6-dihydro-4H- cyclohept [1,2-d] isoxa zole - 8-propionic acid (8, 8- AHCP ), (RS)-alpha-amino-3- hydroxy-7,8-dihydro-6H- cyclohept [1,2-d] isoxazole -4-propionic acid (12, 4- AHCP ), and (RS)-alpha-(methylamino)-3-hydroxy-5-methyl- 4- isoxazolepropionic acid (15, N-Me-AMPA) were shown to be sensitive to (S)-glutamic acid diethyl ester (GDEE), an antagonist at quisqualic acid ( QUIS ) receptors, and insensitive to (RS)-2-amino-5-phosphonovaleric acid ( 2APV ), an antagonist at N-methyl-(R)-aspartic acid (NMDA) receptors. The compounds 4 and 12 proved to be particularly potent agonists at the former class of receptor, assumed to represent physiological glutamic acid receptors. The amino acids (RS)-beta-(2-carboxyphenyl)alanine (19), an analogue of 12, and (RS)-2-(3-carboxyphenyl) glycine were weak GDEE-sensitive excitants with potencies comparable with that of 8. All of the compounds were tested as inhibitors of KA binding. With the exception of 12 and 19, which showed very low affinity for the KA binding sites, the compounds studied were inactive in this in vitro test system.

  DOI：

  10.1021/jm00371a005
• 作为产物：
  描述：

  (RS)-methyl 3-methoxy-4,5,6,7-tetrahydroisoxazolo<5,4-c>pyridine-7-carboxylate hydrobromide 在 氢溴酸 作用下， 以 溶剂黄146 为溶剂， 反应 16.0h， 以83%的产率得到(RS)-methyl 3-hydroxy-4,5,6,7-tetrahydroisoxazolo<5,4-c>pyridine-7-carboxylate hydrobromide
  参考文献：
  名称：

  结构上与ibotenic酸有关的兴奋性氨基酸的合成和结构活性研究。

  摘要：

  以卵磷脂为铅，（RS）-α-氨基-3-羟基-5-甲基异恶唑-4-丙酸（AMPA）和（RS）-3-羟基-4,5,6的类似物，合成了7-四氢异恶唑并[5,4-c]吡啶-7-羧酸（7-HPCA），并通过微电泳技术测试了猫脊髓中神经元的兴奋性，并测试了海藻酸的结合抑制剂。像AMPA和7-HPCA，（RS）-3-羟基-4,5,6,7-四氢异恶唑并[5,4-c]-吡啶-5-羧酸（10，5-HPCA）和（RS）- 3-羟基-5-（溴甲基）异恶唑-4-丙酸（11，ABPA）被证明与假定为生理性谷氨酸受体的中央喹喹酸受体有效且选择性地相互作用。7-HPCA或10的类似物，其中一个或两个酸基均被掩盖，它们作为神经元兴奋剂非常弱或无活性，对兴奋性氨基酸受体没有拮抗作用。通过X射线分析确定了处于结晶状态的7-HPCA的结构。通过1 H NMR光谱确定水溶液中10的优选构象。在这些研究的基础上，显示7-HPCA以及

  DOI：

  10.1021/jm50001a023