3-Methoxy-5-isoxazolessigsaeure-methylester | 4992-22-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-Methoxy-5-isoxazolessigsaeure-methylester
• 英文别名: α-(3-Methoxy-5-isoxazol)-essigsaeure-methylester；3-Methoxy-isoxazol-5-essigsaeure-methylester；(3-methoxy-isoxazol-5-yl)-acetic acid methyl ester；Methyl 2-(3-methoxy-1,2-oxazol-5-yl)acetate；methyl 2-(3-methoxy-1,2-oxazol-5-yl)acetate
• CAS: 4992-22-7
• 化学式: C₇H₉NO₄
• 分子量: 171.153
• InChiKey: MHPALLVGTMCEMC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  12
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  61.6
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-Methoxy-5-isoxazolessigsaeure-methylester 在 吡啶 、 lithium aluminium tetrahydride 、 氢溴酸 、 sodium iodide 作用下， 以 乙醚 、 乙醇 、 丙酮 、 甲苯 为溶剂， 反应 80.75h， 生成 (RS)-α-amino-3-hydroxyisoxazole-5-butyric acid
  参考文献：
  名称：

  Ibotenic Acid Analogues. Synthesis, Molecular Flexibility, and in Vitro Activity of Agonists and Antagonists at Central Glutamic Acid Receptors

  摘要：

  The syntheses of (RS)-alpha-amino-3-hydroxy-5-tert-butyl-4-isoxazolepropionic acid (9, ATPA), (alpha-RS, beta-RS)-alpha-amino-beta-methyl-3-hydroxy-5-isoxazolepropionic acid (8), (RS)-alpha-amino-3-hydroxy-5-isoxazolebutyric acid (15a), and (RS)-alpha-amino-3-hydroxy-5-isoxazolevaleric acid (15b) are described. The compounds were tested in vitro together with (RS)-alpha-amino-3-hydroxy-5-(bromomethyl)-4-isoxazolepropionic acid (ABPA) as inhibitors of the binding of radioactive-labeled (RS)-alpha-amino-3-hydroxy-5-methyl-4-isoxazolepropionic acid (AMPA) to rat brain synaptic membranes. These data were compared with the earlier reported effects of the compounds on single neurons in the feline spinal cord obtained by microelectrophoretic techniques. The three compounds AMPA, ATPA, and ABPA are agonists at the class of receptors assumed to represent a subtype of physiological (S)-glutamic acid (Glu) receptors. Inhibition of [3H]AMPA binding by ATPA was 1 order of magnitude weaker than that of AMPA, in agreement with the relative potency of these compounds in vivo. ABPA proved to be equipotent with AMPA both as an inhibitor of AMPA binding and as a neuronal excitant. The compounds 8, 15a, and 15b have no effect as inhibitors of AMPA binding, in agreement with in vivo studies that have shown that 8 does not affect the firing of central neurons whereas 15a and 15b are antagonists at NMDA receptors, a subpopulation of excitatory receptors not affected by AMPA. Molecular mechanical calculations on AMPA, ATPA, and ABPA using the program MM2 showed that conformations of AMPA, ABPA, and especially ATPA by rotation of the amino acid side chain have energy barriers. A possible receptor-active conformation is suggested.

  DOI：

  10.1021/jm50001a022
• 作为产物：
  描述：

  甲醇 、 (3-bromo-isoxazol-5-yl)-acetic acid; potassium salt 生成 3-Methoxy-5-isoxazolessigsaeure-methylester
  参考文献：
  名称：

  Synthesis of Ibotenic Acid and 3-Deoxyibotenic Acid

  摘要：

  DOI：

  10.1248/cpb.14.89

文献信息

• The synthesis of pantherine and related compounds
  作者：K. Bowden、G. Crank、W. J. Ross

  DOI：10.1039/j39680000172

  日期：——

  One of the active principles of Amanita muscaria, 5-aminomethyl-3-hydroxyisoxazole (I) has been synthesised from 3-bromo-5-methylisoxazole by way of 3-methoxyisoxazole-5-acetic acid (XIII), and from 3-methoxyisoxazole-5-carboxylic acid (XXa) by reduction of its amide with diborane. Analogues of (I) with methyl and ethyl substituents in the 4-position have been prepared similarly from 3-hydroxy-4,5-dimethylisoxazole

  毒蝇伞活性成分之一，5-氨基甲基-3-羟基异恶唑（I）是由3-溴-5-甲基异恶唑通过3-甲氧基异恶唑-5-乙酸（XIII）和3-甲氧基异恶唑-5-羧酸（XXa）合成的。通过用乙硼烷还原酰胺。通过第一种方法类似地由3-羟基-4,5-二甲基异恶唑和4-乙基-3-羟基-5-甲基异恶唑制备了（I）在4-位具有甲基和乙基取代基的类似物。（I）具有5个较长碱性侧链的同系物是通过3-甲氧基异恶唑-5-丙酸（XXIIb）的Curtius反应，以及通过乙硼烷还原3-甲氧基异恶唑-5-乙酸的酰胺而制得的（I）同源物XIII）和3-甲氧基-4-甲基异恶唑-5-乙酸（XXIb）。
• Acylation of 5-isoxazolylalkyl carbanions: synthesis of bis- and tris-isoxazole compounds
  作者：Tadasu Tanaka、Michihiko Miyazaki、Ikuo Iijima

  DOI：10.1039/c3973000233a

  日期：——

  Bis- and tris-isoxazole compounds have been prepared from 3,5-dimethylisoxazole.

  由3,5-二甲基异恶唑制备了双异和三异恶唑化合物。
• Ibotenic Acid Analogues. Synthesis, Molecular Flexibility, and in Vitro Activity of Agonists and Antagonists at Central Glutamic Acid Receptors
  作者：Jørn Lauridsen、Tage Honoré、Povl Krogsgaard-Larsen

  DOI：10.1021/jm50001a022

  日期：1985.5

  The syntheses of (RS)-alpha-amino-3-hydroxy-5-tert-butyl-4-isoxazolepropionic acid (9, ATPA), (alpha-RS, beta-RS)-alpha-amino-beta-methyl-3-hydroxy-5-isoxazolepropionic acid (8), (RS)-alpha-amino-3-hydroxy-5-isoxazolebutyric acid (15a), and (RS)-alpha-amino-3-hydroxy-5-isoxazolevaleric acid (15b) are described. The compounds were tested in vitro together with (RS)-alpha-amino-3-hydroxy-5-(bromomethyl)-4-isoxazolepropionic acid (ABPA) as inhibitors of the binding of radioactive-labeled (RS)-alpha-amino-3-hydroxy-5-methyl-4-isoxazolepropionic acid (AMPA) to rat brain synaptic membranes. These data were compared with the earlier reported effects of the compounds on single neurons in the feline spinal cord obtained by microelectrophoretic techniques. The three compounds AMPA, ATPA, and ABPA are agonists at the class of receptors assumed to represent a subtype of physiological (S)-glutamic acid (Glu) receptors. Inhibition of [3H]AMPA binding by ATPA was 1 order of magnitude weaker than that of AMPA, in agreement with the relative potency of these compounds in vivo. ABPA proved to be equipotent with AMPA both as an inhibitor of AMPA binding and as a neuronal excitant. The compounds 8, 15a, and 15b have no effect as inhibitors of AMPA binding, in agreement with in vivo studies that have shown that 8 does not affect the firing of central neurons whereas 15a and 15b are antagonists at NMDA receptors, a subpopulation of excitatory receptors not affected by AMPA. Molecular mechanical calculations on AMPA, ATPA, and ABPA using the program MM2 showed that conformations of AMPA, ABPA, and especially ATPA by rotation of the amino acid side chain have energy barriers. A possible receptor-active conformation is suggested.
• Synthesis of Ibotenic Acid and 3-Deoxyibotenic Acid
  作者：Kenzo Sirakawa、Osami Aki、Susumu Tsushima、Kazuo Konishi

  DOI：10.1248/cpb.14.89

  日期：——