5-(aminomethyl)-N-(3,4-dichlorobenzyl)-4-(4-methoxyphenyl)-6-methylpicolinamide | 1253518-67-0

• 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
• 英文名称: 5-(aminomethyl)-N-(3,4-dichlorobenzyl)-4-(4-methoxyphenyl)-6-methylpicolinamide
• 英文别名: 5-(aminomethyl)-N-[(3,4-dichlorophenyl)methyl]-4-(4-methoxyphenyl)-6-methylpyridine-2-carboxamide
• CAS: 1253518-67-0
• 化学式: C₂₂H₂₁Cl₂N₃O₂
• 分子量: 430.334
• InChiKey: GWTAEZPFUNDLNK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  29
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  77.2
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  5-cyano-4-(4-methoxyphenyl)-6-methylpyridine-2-carboxylic acid 在 10% palladium on activated carbon 、 benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate 、 水 、 氢气 、 溶剂黄146 、 三乙胺 、 三氟乙酸 作用下， 以 1,4-二氧六环 、 二氯甲烷 、 水 为溶剂， 反应 41.0h， 生成 5-(aminomethyl)-N-(3,4-dichlorobenzyl)-4-(4-methoxyphenyl)-6-methylpicolinamide
  参考文献：
  名称：

  Design, Synthesis, and in Vitro Evaluation of Novel Aminomethyl-pyridines as DPP-4 Inhibitors

  摘要：

  A collection of novel aminomethyl-pyridines was designed, synthesized, and investigated as potential inhibitors of DPP-4. Optimization of the screening hit afforded a number of 5-aminomethyl-pyridines with inhibitory activity in the nanomolar range. Selected DPP-4 inhibitors were further evaluated for their selectivity over the closely related peptidase DPP-8. 5-Aminomethyl-4-(2,4-dichlorophenyl)-6-methyl-pyridine-2-carboxylic acid cyanomethyl-amide showed high potency and excellent DPP-4 selectivity [IC50: 10 (DPP-4) and 6600 nM (DPP-8)] and no toxicity in mammalian cell culture.

  DOI：

  10.1021/ml100200c

文献信息

• Design, Synthesis, and in Vitro Evaluation of Novel Aminomethyl-pyridines as DPP-4 Inhibitors
  作者：Katarzyna Kaczanowska、Karl-Heinz Wiesmüller、Arnaud-Pierre Schaffner

  DOI：10.1021/ml100200c

  日期：2010.12.9

  A collection of novel aminomethyl-pyridines was designed, synthesized, and investigated as potential inhibitors of DPP-4. Optimization of the screening hit afforded a number of 5-aminomethyl-pyridines with inhibitory activity in the nanomolar range. Selected DPP-4 inhibitors were further evaluated for their selectivity over the closely related peptidase DPP-8. 5-Aminomethyl-4-(2,4-dichlorophenyl)-6-methyl-pyridine-2-carboxylic acid cyanomethyl-amide showed high potency and excellent DPP-4 selectivity [IC50: 10 (DPP-4) and 6600 nM (DPP-8)] and no toxicity in mammalian cell culture.