4-(2,4-dichlorophenyl)-6-[(1,3-dioxoisoindolin-2-yl)methyl]-2-methylpyridine-3-carboxamide | 1253519-31-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: 4-(2,4-dichlorophenyl)-6-[(1,3-dioxoisoindolin-2-yl)methyl]-2-methylpyridine-3-carboxamide
• 英文别名: 4-(2,4-Dichlorophenyl)-6-[(1,3-dioxoisoindol-2-yl)methyl]-2-methylpyridine-3-carboxamide
• CAS: 1253519-31-1
• 化学式: C₂₂H₁₅Cl₂N₃O₃
• 分子量: 440.285
• InChiKey: UPKLDXSUUGEVFK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  30
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  93.4
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-(2,4-dichlorophenyl)-6-[(1,3-dioxoisoindolin-2-yl)methyl]-2-methylpyridine-3-carboxamide 在 potassium hydroxide 作用下， 以 水 为溶剂， 反应 4.0h， 生成 6-(Aminomethyl)-4-(2,4-dichlorophenyl)-2-methylnicotinamide
  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
• 作为产物：
  描述：

  4-(2,4-dichlorophenyl)-5-cyano-6-methylpyridine-2-carboxylic acid 在 sodium tetrahydroborate 、 氯化亚砜 、 potassium tert-butylate 、 水 、 三乙胺 作用下， 以 四氢呋喃 、 水 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 24.0h， 生成 4-(2,4-dichlorophenyl)-6-[(1,3-dioxoisoindolin-2-yl)methyl]-2-methylpyridine-3-carboxamide
  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

• TOMM6-INTERACTING EXTRACTS AND COMPOUNDS FOR USE IN THE TREATMENT AND PROPHYLAXIS OF NERVOUS SYSTEM DISEASES, ATHEROSCLEROSIS, HEPATITIS B INFECTION AND HUMAN PAPILLOMA VIRUS (HPV) INFECTION
  申请人：ETH Zurich

  公开号：EP3801507A2

  公开（公告）日：2021-04-14