5'-<<(4-ethoxyphenyl)amino>carbonyl><2,2'-bipyridine>-5-carboxylic acid

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 5'-<<(4-ethoxyphenyl)amino>carbonyl><2,2'-bipyridine>-5-carboxylic acid
• 英文别名: 5''-(4-Ethoxy-phenylcarbamoyl)-[2,2'']bipyridinyl-5-carboxylic acid；6-[5-[(4-ethoxyphenyl)carbamoyl]pyridin-2-yl]pyridine-3-carboxylic acid
• 化学式: C₂₀H₁₇N₃O₄
• 分子量: 363.373
• InChiKey: UBYXPZXRXSCDOB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  27
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  101
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  对乙氧基苯胺 在 sodium hydroxide 、 三乙胺 作用下， 以 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 6.0h， 生成 5'-<<(4-ethoxyphenyl)amino>carbonyl><2,2'-bipyridine>-5-carboxylic acid
  参考文献：
  名称：

  Novel inhibitors of prolyl 4-hydroxylase. 5. The intriguing structure-activity relationships seen with 2,2'-bipyridine and its 5,5'-dicarboxylic acid derivatives

  摘要：

  Members of a series of 2,2'-bipyridines have been synthesized and tested as inhibitors of prolyl hydroxylase (EC 1.14.11.2). The structure-activity relationships seen with [2,2'-bipyridine]-5-carboxylic acid (4) closely resemble those of pyridine-2-carboxylic acid (2). Accordingly, [2,2'-bipyridine]-5,5'-dicarboxylic acid (11, IC50 = 0.19 mu M) is the most potent inhibitor of its type yet reported. However, 2,2'-bipyridines lacking a 5-carboxylate are poor inhibitors. These contrasting structure-activity relationships are discussed in terms of net anionic charge, iron chelation, and the availability of alternative putative binding modes at a single binding site in each catalytic subunit.

  DOI：

  10.1021/jm00076a014

文献信息

• Hales Neil J., Beattie John F., J. Med. Chem, 36 (1993) N 24, S 3853- 3858
  作者：Hales Neil J., Beattie John F.

  DOI：——

  日期：——
• Novel inhibitors of prolyl 4-hydroxylase. 5. The intriguing structure-activity relationships seen with 2,2'-bipyridine and its 5,5'-dicarboxylic acid derivatives
  作者：Neil J. Hales、John F. Beattie

  DOI：10.1021/jm00076a014

  日期：1993.11

  Members of a series of 2,2'-bipyridines have been synthesized and tested as inhibitors of prolyl hydroxylase (EC 1.14.11.2). The structure-activity relationships seen with [2,2'-bipyridine]-5-carboxylic acid (4) closely resemble those of pyridine-2-carboxylic acid (2). Accordingly, [2,2'-bipyridine]-5,5'-dicarboxylic acid (11, IC50 = 0.19 mu M) is the most potent inhibitor of its type yet reported. However, 2,2'-bipyridines lacking a 5-carboxylate are poor inhibitors. These contrasting structure-activity relationships are discussed in terms of net anionic charge, iron chelation, and the availability of alternative putative binding modes at a single binding site in each catalytic subunit.