5-(4-chloromethyl-3-isopropoxy-5-isoxazolyl)-2-ethyl-2H-tetrazole | 852567-82-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5-(4-chloromethyl-3-isopropoxy-5-isoxazolyl)-2-ethyl-2H-tetrazole
• 英文别名: 4-(Chloromethyl)-5-(2-ethyltetrazol-5-yl)-3-propan-2-yloxy-1,2-oxazole
• CAS: 852567-82-9
• 化学式: C₁₀H₁₄ClN₅O₂
• 分子量: 271.706
• InChiKey: GBJJOJNKQNCVRR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  78.9
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  5-(4-chloromethyl-3-isopropoxy-5-isoxazolyl)-2-ethyl-2H-tetrazole 在 盐酸 、 sodium hydride 、 溶剂黄146 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 36.0h， 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 、 potassium carbonate 、 三氯氧磷 作用下， 以 四氢呋喃 、 乙二醇二甲醚 、 丙酮 为溶剂， 反应 92.17h， 生成 5-(4-chloromethyl-3-isopropoxy-5-isoxazolyl)-2-ethyl-2H-tetrazole
  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