methyl 2-acetamido-3-[3-isopropoxy-5-(2-ethyl-2H-5-tetrazolyl)-4-isoxazolyl]-2-(methoxycarbonyl)propionate | 852567-83-0

• 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: methyl 2-acetamido-3-[3-isopropoxy-5-(2-ethyl-2H-5-tetrazolyl)-4-isoxazolyl]-2-(methoxycarbonyl)propionate
• 英文别名: Dimethyl 2-acetamido-2-[[5-(2-ethyltetrazol-5-yl)-3-propan-2-yloxy-1,2-oxazol-4-yl]methyl]propanedioate
• CAS: 852567-83-0
• 化学式: C₁₇H₂₄N₆O₇
• 分子量: 424.414
• InChiKey: BATTXYRRIWVVLJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  30
• 可旋转键数：
  11
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  161
• 氢给体数：
  1
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  methyl 2-acetamido-3-[3-isopropoxy-5-(2-ethyl-2H-5-tetrazolyl)-4-isoxazolyl]-2-(methoxycarbonyl)propionate 在 盐酸 、 溶剂黄146 作用下， 反应 11.0h， 生成 (RS)-2-amino-3-[3-hydroxy-5-(2-ethyl-2H-5-tetrazolyl)-4-isoxazolyl]propionic acid hydrochloride
  参考文献：
  名称：

  Convergent Synthesis and Pharmacology of Substituted Tetrazolyl-2-amino-3-(3-hydroxy-5-methyl-4-isoxazolyl)propionic acid Analogues

  摘要：

  The synthesis and pharmacological characterization of 1- and 2-alkyltetrazolyl analogues of (RS)-2-amino-3-[3-hydroxy-5-(2-methyl-2H-5-tetrazolyl)-4-isoxazolyl]propionic acid (2-Me-Tet-AMPA), a highly potent and selective agonist at AMPA receptors, are presented. A shorter and more convergent synthetic route than previously described, employing a new method for introducing the amino acid moiety, was developed for these derivatives. The 2-substituted isomers were selective agonists, and their activity correlated inversely with the size of the substituent. Structural explanations of the structure-activity relationship are provided.

  DOI：

  10.1021/jm050014l
• 作为产物：
  描述：

  methyl 3-isopropoxyisoxazole-5-carboxylate 在 ammonium hydroxide 、 正丁基锂 、 氯化亚砜 、 sodium azide 、 三乙胺盐酸盐 、 sodium hydride 、 potassium carbonate 、 三氯氧磷 作用下， 以 四氢呋喃 、 乙二醇二甲醚 、 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 反应 117.17h， 生成 methyl 2-acetamido-3-[3-isopropoxy-5-(2-ethyl-2H-5-tetrazolyl)-4-isoxazolyl]-2-(methoxycarbonyl)propionate
  参考文献：
  名称：

  Convergent Synthesis and Pharmacology of Substituted Tetrazolyl-2-amino-3-(3-hydroxy-5-methyl-4-isoxazolyl)propionic acid Analogues

  摘要：

  The synthesis and pharmacological characterization of 1- and 2-alkyltetrazolyl analogues of (RS)-2-amino-3-[3-hydroxy-5-(2-methyl-2H-5-tetrazolyl)-4-isoxazolyl]propionic acid (2-Me-Tet-AMPA), a highly potent and selective agonist at AMPA receptors, are presented. A shorter and more convergent synthetic route than previously described, employing a new method for introducing the amino acid moiety, was developed for these derivatives. The 2-substituted isomers were selective agonists, and their activity correlated inversely with the size of the substituent. Structural explanations of the structure-activity relationship are provided.

  DOI：

  10.1021/jm050014l

文献信息

• Convergent Synthesis and Pharmacology of Substituted Tetrazolyl-2-amino-3-(3-hydroxy-5-methyl-4-isoxazolyl)propionic acid Analogues
  作者：Stine B. Vogensen、Rasmus P. Clausen、Jeremy R. Greenwood、Tommy N. Johansen、Darryl S. Pickering、Birgitte Nielsen、Bjarke Ebert、Povl Krogsgaard-Larsen

  DOI：10.1021/jm050014l

  日期：2005.5.1

  The synthesis and pharmacological characterization of 1- and 2-alkyltetrazolyl analogues of (RS)-2-amino-3-[3-hydroxy-5-(2-methyl-2H-5-tetrazolyl)-4-isoxazolyl]propionic acid (2-Me-Tet-AMPA), a highly potent and selective agonist at AMPA receptors, are presented. A shorter and more convergent synthetic route than previously described, employing a new method for introducing the amino acid moiety, was developed for these derivatives. The 2-substituted isomers were selective agonists, and their activity correlated inversely with the size of the substituent. Structural explanations of the structure-activity relationship are provided.