5-(α-carboxyphenethyl)pyridine-2-carboxylic acid | 138834-56-7

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 苯丙酸
• 英文名称: 5-(α-carboxyphenethyl)pyridine-2-carboxylic acid
• 英文别名: 5-(1-Carboxy-2-phenyl-ethyl)-pyridine-2-carboxylic acid；5-(1-carboxy-2-phenylethyl)pyridine-2-carboxylic acid
• CAS: 138834-56-7
• 化学式: C₁₅H₁₃NO₄
• 分子量: 271.273
• InChiKey: ODAGOQCTPRRXEW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  87.5
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  (2-carboxy-5-pyridyl)acetic acid dimethyl ester 在 sodium hydroxide 、 lithium diisopropyl amide 作用下， 以 甲醇 为溶剂， 反应 3.33h， 生成 5-(α-carboxyphenethyl)pyridine-2-carboxylic acid
  参考文献：
  名称：

  Novel inhibitors of prolyl 4-hydroxylase

  摘要：

  A series of 5-acyl sulfonamides derived from pyridine-2,5-dicarboxylic acid (15) has been prepared and several members of this series have been shown to be more potent, in vitro, as inhibitors of prolyl 4-hydroxylase than 15. Several chain-extended pyridinedicarboxylic acids have also been prepared and shown to be potent inhibitors of prolyl 4-hydroxylase. The structure-activity in both these series is discussed. The results indicate that the 5-carboxylic acid binding site, in the enzyme, can accept a carboxylic acid or an acyl sulfonamide equally well. This indicates a much greater degree of freedom in this distal carboxylic acid binding site than is predicted by the current theorical model of the active site.

  DOI：

  10.1021/jm00083a001