5-(3-isopropoxy-5-isoxazolyl)-1H-tetrazole | 852567-73-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5-(3-isopropoxy-5-isoxazolyl)-1H-tetrazole
• 英文别名: 3-propan-2-yloxy-5-(2H-tetrazol-5-yl)-1,2-oxazole
• CAS: 852567-73-8
• 化学式: C₇H₉N₅O₂
• mdl: MFCD09030710
• 分子量: 195.181
• InChiKey: YKXXTEMETYQRNH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.428
• 拓扑面积：
  89.7
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  5-(3-isopropoxy-5-isoxazolyl)-1H-tetrazole 在 正丁基锂 、 potassium carbonate 作用下， 以 四氢呋喃 、 丙酮 为溶剂， 反应 19.17h， 生成 5-(4-hydroxymethyl-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
• 作为产物：
  描述：

  methyl 3-isopropoxyisoxazole-5-carboxylate 在 ammonium hydroxide 、 sodium azide 、 三乙胺盐酸盐 、 三氯氧磷 作用下， 以 乙二醇二甲醚 为溶剂， 反应 69.0h， 生成 5-(3-isopropoxy-5-isoxazolyl)-1H-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

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.