tert-butyl (RS)-2-tert-butoxycarbonylamino-3-[3-isopropoxy-5(1-isopropyl-1H-5-tetrazolyl)-4-isoxazolyl]propionate | 852567-91-0

• 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: tert-butyl (RS)-2-tert-butoxycarbonylamino-3-[3-isopropoxy-5(1-isopropyl-1H-5-tetrazolyl)-4-isoxazolyl]propionate
• 英文别名: Tert-butyl 2-[(2-methylpropan-2-yl)oxycarbonylamino]-3-[3-propan-2-yloxy-5-(1-propan-2-yltetrazol-5-yl)-1,2-oxazol-4-yl]propanoate
• CAS: 852567-91-0
• 化学式: C₂₂H₃₆N₆O₆
• 分子量: 480.564
• InChiKey: NCFYUHBARSAPOI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  34
• 可旋转键数：
  12
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  144
• 氢给体数：
  1
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  tert-butyl (RS)-2-tert-butoxycarbonylamino-3-[3-isopropoxy-5(1-isopropyl-1H-5-tetrazolyl)-4-isoxazolyl]propionate 在 氢溴酸 作用下， 反应 0.33h， 以36%的产率得到2-Amino-3-[3-hydroxy-5-(1-isopropyl-1H-tetrazol-5-yl)-isoxazol-4-yl]-propionic acid
  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 、 sodium azide 、 三乙胺盐酸盐 、 三氯氧磷 作用下， 以 四氢呋喃 、 乙二醇二甲醚 、 甲苯 为溶剂， 反应 90.33h， 生成 tert-butyl (RS)-2-tert-butoxycarbonylamino-3-[3-isopropoxy-5(1-isopropyl-1H-5-tetrazolyl)-4-isoxazolyl]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