N-(2’,4’-dichlorophenylethyl)-2-bromoacetamide

• 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-(2’,4’-dichlorophenylethyl)-2-bromoacetamide
• 英文别名: 2-bromo-N-(2,4-dichlorophenethyl)acetamide；2-bromo-N-[2-(2,4-dichlorophenyl)ethyl]acetamide
• 化学式: C₁₀H₁₀BrCl₂NO
• 分子量: 311.005
• InChiKey: AORAKWJHQOYXKG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  N-(2’,4’-dichlorophenylethyl)-2-bromoacetamide 在 palladium 10% on activated carbon 、 氢气 、 sodium hydride 作用下， 以 四氢呋喃 、 甲醇 、 1,2-二氯乙烷 、 mineral oil 为溶剂， 20.0~140.0 ℃ 、101.33 kPa 条件下， 反应 58.83h， 生成 N-(2',4'-dichlorophenethyl)-2-(3"-(benzylamino)-2"-oxopyridin-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
• 作为产物：
  描述：

  2,4-二氯苯酚呋喃 、 溴乙酰溴 在 4-二甲氨基吡啶 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 以62%的产率得到N-(2’,4’-dichlorophenylethyl)-2-bromoacetamide
  参考文献：
  名称：

  新型19 F磁共振敏感蛋白酪氨酸磷酸酶抑制剂的设计，合成和评估† ‡

  摘要：

  氟对于药物化学和成像技术都是极具吸引力的元素。为了促进针对蛋白质酪氨酸磷酸酶（PTP）的药物发现和对氟的成像指导PTP研究，通过基于结构的聚焦文库策略发现了几种高效和19 F MR敏感的PTP抑制剂。

  DOI：

  10.1039/c6md00277c

文献信息

• Design, synthesis and evaluation of novel ¹⁹F magnetic resonance sensitive protein tyrosine phosphatase inhibitors
  作者：Yu Li、Guiquan Xia、Qi Guo、Li Wu、Shizhen Chen、Zhigang Yang、Wei Wang、Zhong-Yin Zhang、Xin Zhou、Zhong-Xing Jiang

  DOI：10.1039/c6md00277c

  日期：——

  Fluorine is a highly attractive element for both medicinal chemistry and imaging technologies. To facilitate protein tyrosine phosphatase (PTP)-targeted drug discovery and imaging-guided PTP research on fluorine, several highly potent and 19F MR sensitive PTP inhibitors were discovered through a structure-based focused library strategy.

  氟对于药物化学和成像技术都是极具吸引力的元素。为了促进针对蛋白质酪氨酸磷酸酶（PTP）的药物发现和对氟的成像指导PTP研究，通过基于结构的聚焦文库策略发现了几种高效和19 F MR敏感的PTP抑制剂。
• 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.