2-氯-4-(1-乙基丙氧基)-6-甲基烟酸 | 1013933-36-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 中文名称: 2-氯-4-(1-乙基丙氧基)-6-甲基烟酸
• 英文名称: 2-chloro-4-(1-ethylpropoxy)-6-methylnicotinic acid
• 英文别名: 2-chloro-6-methyl-4-pentan-3-yloxypyridine-3-carboxylic acid
• CAS: 1013933-36-2
• 化学式: C₁₂H₁₆ClNO₃
• 分子量: 257.717
• InChiKey: FUUGHOLQDLQEKQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  59.4
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-氯-4-(1-乙基丙氧基)-6-甲基烟酸 、 2,4,6-三甲基苯胺 在 铜 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 以29.4%的产率得到4-(1-ethylpropoxy)-6-methyl-2-(2,4,6-trimethylphenylamino)nicotinic acid
  参考文献：
  名称：

  2-Aryloxy-4-alkylaminopyridines: Discovery of Novel Corticotropin-Releasing Factor 1 Antagonists

  摘要：

  An orally active clinical candidate of corticotropin-releasing factor 1 (CRF(1)) antagonist 1 showed a significant positive food effect in dog and human after oral administration. Efforts to address the food effect issue led us to explore and discover compounds in series 2 as orally active CRF(1) receptor antagonists, in which some compounds showed improved physicochemical properties while retaining desired pharmacological properties. Compound 3a (CP-376395) was selected for further development, due not only to its reduced food effects but also its greater efficacy in CNS models. Compound 3a was advanced to the clinic. The synthesis of representative potential candidates and their in vitro, ex vivo, and in vivo data are described.

  DOI：

  10.1021/jm070579c
• 作为产物：
  描述：

  2-氯-4-(1-乙基丙氧基)-6-甲基烟酸甲酯 在 sodium hydroxide 作用下， 以 甲醇 、 水 为溶剂， 反应 3.0h， 以86%的产率得到2-氯-4-(1-乙基丙氧基)-6-甲基烟酸
  参考文献：
  名称：

  2-Aryloxy-4-alkylaminopyridines: Discovery of Novel Corticotropin-Releasing Factor 1 Antagonists

  摘要：

  An orally active clinical candidate of corticotropin-releasing factor 1 (CRF(1)) antagonist 1 showed a significant positive food effect in dog and human after oral administration. Efforts to address the food effect issue led us to explore and discover compounds in series 2 as orally active CRF(1) receptor antagonists, in which some compounds showed improved physicochemical properties while retaining desired pharmacological properties. Compound 3a (CP-376395) was selected for further development, due not only to its reduced food effects but also its greater efficacy in CNS models. Compound 3a was advanced to the clinic. The synthesis of representative potential candidates and their in vitro, ex vivo, and in vivo data are described.

  DOI：

  10.1021/jm070579c

文献信息

• 2-Aryloxy-4-alkylaminopyridines: Discovery of Novel Corticotropin-Releasing Factor 1 Antagonists
  作者：Yuhpyng L. Chen、R. Scott Obach、John Braselton、Michael L. Corman、James Forman、Jody Freeman、Randall J. Gallaschun、Robert Mansbach、Anne W. Schmidt、Jeffrey S. Sprouse、F. David Tingley, III、Elizabeth Winston、David W. Schulz

  DOI：10.1021/jm070579c

  日期：2008.3.13

  An orally active clinical candidate of corticotropin-releasing factor 1 (CRF(1)) antagonist 1 showed a significant positive food effect in dog and human after oral administration. Efforts to address the food effect issue led us to explore and discover compounds in series 2 as orally active CRF(1) receptor antagonists, in which some compounds showed improved physicochemical properties while retaining desired pharmacological properties. Compound 3a (CP-376395) was selected for further development, due not only to its reduced food effects but also its greater efficacy in CNS models. Compound 3a was advanced to the clinic. The synthesis of representative potential candidates and their in vitro, ex vivo, and in vivo data are described.