N-(3",4"-dichlorobenzyl)-2-[2'-oxo-3'-[(pyridin-2‴-ylmethyl)amino]pyridin-1'(2H)-yl]acetamide

• 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: N-(3",4"-dichlorobenzyl)-2-[2'-oxo-3'-[(pyridin-2‴-ylmethyl)amino]pyridin-1'(2H)-yl]acetamide
• 英文别名: N-[(3,4-dichlorophenyl)methyl]-2-[2-oxo-3-(pyridin-2-ylmethylamino)pyridin-1-yl]acetamide
• 化学式: C₂₀H₁₈Cl₂N₄O₂
• 分子量: 417.295
• InChiKey: BFOFAZBFBRDVQT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  28
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  74.3
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  吡啶-2-甲醛 、 乙基(3-氨基-2-氧代-1(2H)-吡啶基)乙酸酯 以 二氯甲烷 为溶剂， 反应 22.0h， 生成 N-(3",4"-dichlorobenzyl)-2-[2'-oxo-3'-[(pyridin-2‴-ylmethyl)amino]pyridin-1'(2H)-yl]acetamide
  参考文献：
  名称：

  2-Oxo-1,2-dihydropyridinyl-3-yl amide-based GPa inhibitors: Design, synthesis and structure-activity relationship study

  摘要：

  Glycogen phosphorylase (GP), which plays a crucial role in the conversion of glycogen to glucose-1-phosphate, is a target for therapeutic intervention in diabetes. In this study, we report the design and synthesis of 29 new derivatives of 2-oxo-1,2-dihydro pyridin-3-yl amides, as potential inhibitors of GP. The hit rate (45%) was high with 13 compounds inhibiting GPa (between 33% at 4.40 mM and an IC50 of 1.92 μM). Two lead compounds were identified as compounds exhibiting good GPa inhibition (IC50 = 2.1 and 1.92 μM). SAR analysis of these compounds revealed sensitivity of GPa to the length of the 2-oxo-1,2-dihydro pyridin-3-yl amide derivative and a preference for inclusion of a 3,4-dichlorobenzyl moiety.

  DOI：

  10.1016/j.ejmech.2016.01.031

文献信息

• 2-Oxo-1,2-dihydropyridinyl-3-yl amide-based GPa inhibitors: Design, synthesis and structure-activity relationship study
  作者：Wendy A. Loughlin、Ian D. Jenkins、N. David Karis、Stephanie S. Schweiker、Peter C. Healy

  DOI：10.1016/j.ejmech.2016.01.031

  日期：2016.3

  Glycogen phosphorylase (GP), which plays a crucial role in the conversion of glycogen to glucose-1-phosphate, is a target for therapeutic intervention in diabetes. In this study, we report the design and synthesis of 29 new derivatives of 2-oxo-1,2-dihydro pyridin-3-yl amides, as potential inhibitors of GP. The hit rate (45%) was high with 13 compounds inhibiting GPa (between 33% at 4.40 mM and an IC50 of 1.92 μM). Two lead compounds were identified as compounds exhibiting good GPa inhibition (IC50 = 2.1 and 1.92 μM). SAR analysis of these compounds revealed sensitivity of GPa to the length of the 2-oxo-1,2-dihydro pyridin-3-yl amide derivative and a preference for inclusion of a 3,4-dichlorobenzyl moiety.