N,N-diethyl-[3-cyano-4-(4-methylphenyl)-4-oxo]butanamide | 386298-13-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: N,N-diethyl-[3-cyano-4-(4-methylphenyl)-4-oxo]butanamide
• 英文别名: 3-cyano-N,N-diethyl-4-oxo-4-p-tolylbutanamide
• CAS: 386298-13-1
• 化学式: C₁₆H₂₀N₂O₂
• 分子量: 272.347
• InChiKey: GSEQUPJLEQCJKB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.58
• 重原子数：
  20.0
• 可旋转键数：
  6.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  61.17
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  N,N-diethyl-[3-cyano-4-(4-methylphenyl)-4-oxo]butanamide 在 一水合肼 、 溶剂黄146 作用下， 以 乙醇 、 溶剂黄146 为溶剂， 反应 6.0h， 生成
  参考文献：
  名称：

  2-Arylpyrazolo[1,5-a]pyrimidin-3-yl acetamides. New potent and selective peripheral benzodiazepine receptor ligands

  摘要：

  A new class of N,N-diethyl-(2-arylpyrazolo[1,5-a]pyrimidin-3-yl)acetamides (3f-y), as azaisosters of Alpidem, was prepared following a novel synthetic method and their affinities for both the peripheral (PBR) and the central (CBR) benzodiazepine receptors were evaluated. Binding assays were carried out using both [H-3]PK 11195 and [H-3]Ro 5-4864 as radioligands for PBR, whereas [H-3]Ro 15-1788 was used for CBR, in rat kidney and rat cortex, respectively. The tested compounds exhibited a broad range of binding affinities from as low as 0.76 nM to inactivity and most of them proved to be high selective ligands for PBR. The preliminary SAR studies suggested some of the structural features required for high affinity and selectivity; particularly the substituents on the pyrimidine moiety seemed to play an important role in PBR versus CBR selectivity. A subset of the highest affinity compounds was also tested for their ability to stimulate steroid biosynthesis in C6 glioma rat cells and some of these were found to increase pregnenolone formation with potency similar to Ro 5-4864 and PK 11195. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(01)00192-4
• 作为产物：
  描述：

  N,N-二乙基-2-氯乙酰胺 、 对甲苯酰乙腈 在 potassium iodide 、 sodium hydroxide 作用下， 以 乙醇 、 水 为溶剂， 反应 0.5h， 以40%的产率得到N,N-diethyl-[3-cyano-4-(4-methylphenyl)-4-oxo]butanamide
  参考文献：
  名称：

  Microwave-assisted organic synthesis of a high-affinity pyrazolo-pyrimidinyl TSPO ligand

  摘要：

  We herein report a dramatically improved total synthesis of the high-affinity translocator protein (TSPO) ligand DPA-714, featuring microwave-assisted organic synthesis (MAOS). Compared with previously described approaches, our novel MAOS method dramatically reduces overall reaction time without adversely effecting reaction yields. We envision that the described MAOS protocol may be suitably applied to high-throughput, diversity-oriented synthesis of novel compounds based on the pyrazolo-pyrimidinyl scaffold. Such an approach could accelerate the development of focused libraries of novel TSPO ligands with potential for future development as molecular imaging and therapeutic agents. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2010.06.074