[4-(4-oxopiperidin-1-yl)benzyloxy]acetic acid | 340756-85-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: [4-(4-oxopiperidin-1-yl)benzyloxy]acetic acid
• 英文别名: 2-[[4-(4-Oxopiperidin-1-yl)phenyl]methoxy]acetic acid
• CAS: 340756-85-6
• 化学式: C₁₄H₁₇NO₄
• 分子量: 263.293
• InChiKey: WQLRJZUMCGAJAV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  66.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N-[5-((1R)-2-amino-1-hydroxy-ethyl)-2-hydroxy-phenyl]-methanesulfonamide 、 [4-(4-oxopiperidin-1-yl)benzyloxy]acetic acid 在 10percent Pd/C 氢气 、 溶剂黄146 作用下， 以 乙醇 为溶剂， 以45%的产率得到(4-{4-[(2R)-2-hydroxy-2-(4-hydroxy-3-methanesulfonylamino-phenyl)-ethylamino]-piperidin-1-yl}-benzyloxy)-acetic acid
  参考文献：
  名称：

  (4-Piperidin-1-yl)phenyl Amides:  Potent and Selective Human β₃ Agonists

  摘要：

  In search of potent and selective human beta (3) agonists as potential drugs for the treatment of human obesity and type II diabetes, a series of (4-piperidin-1-yl)phenyl amides was prepared and evaluated for their biological activity on the human beta (3)-adrenergic receptor. The leucine derivative 26e and the reverse amide 33b were found to be the two most potent and selective compounds in this study. With EC50 values of 0.008 and 0.009 muM, respectively, at the beta (3) receptor, nearly completely abolished intrinsic activity at either the beta (1) or beta (2) receptor, and significant thermogenesis effects on human beta (3)-adrenergic receptor transgenic mice, 26e and 33b are among the most potent and selective human beta (3) agonists known to date.

  DOI：

  10.1021/jm000544b
• 作为产物：
  描述：

  [4-(1,4-dioxa-8-azaspiro[4.5]dec-8-yl)phenyl]methanol 在 盐酸 、 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 7.0h， 生成 [4-(4-oxopiperidin-1-yl)benzyloxy]acetic acid
  参考文献：
  名称：

  (4-Piperidin-1-yl)phenyl Amides:  Potent and Selective Human β₃ Agonists

  摘要：

  In search of potent and selective human beta (3) agonists as potential drugs for the treatment of human obesity and type II diabetes, a series of (4-piperidin-1-yl)phenyl amides was prepared and evaluated for their biological activity on the human beta (3)-adrenergic receptor. The leucine derivative 26e and the reverse amide 33b were found to be the two most potent and selective compounds in this study. With EC50 values of 0.008 and 0.009 muM, respectively, at the beta (3) receptor, nearly completely abolished intrinsic activity at either the beta (1) or beta (2) receptor, and significant thermogenesis effects on human beta (3)-adrenergic receptor transgenic mice, 26e and 33b are among the most potent and selective human beta (3) agonists known to date.

  DOI：

  10.1021/jm000544b