N,N-diethyl-[3-cyano-4-(4-fluorophenyl)-4-oxo]butanamide | 386298-12-0

• 英文名称: N,N-diethyl-[3-cyano-4-(4-fluorophenyl)-4-oxo]butanamide
• 英文别名: 3-cyano-N,N-diethyl-4-(4-fluorophenyl)-4-oxobutanamide
• CAS: 386298-12-0
• 化学式: C₁₅H₁₇FN₂O₂
• 分子量: 276.311
• InChiKey: VSQQJNFDLMSGRI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.41
• 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：
  0.4
• 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-fluorophenyl)-4-oxo]butanamide 在 一水合肼 、 溶剂黄146 作用下， 以 乙醇 为溶剂， 反应 10.0h， 生成 N,N-Diethyl-2-[2-(4-fluoro-phenyl)-5-methyl-pyrazolo[1,5-a]pyrimidin-3-yl]-acetamide
  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：

  4-氟苯甲酰基乙腈 、 N,N-二乙基-2-氯乙酰胺 在 sodium hydroxide 、 sodium iodide 作用下， 以 乙醇 为溶剂， 反应 8.0h， 以13%的产率得到N,N-diethyl-[3-cyano-4-(4-fluorophenyl)-4-oxo]butanamide
  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

文献信息

• A Facile Radiolabeling of [¹⁸F]FDPA via Spirocyclic Iodonium Ylides: Preliminary PET Imaging Studies in Preclinical Models of Neuroinflammation
  作者：Lu Wang、Ran Cheng、Masayuki Fujinaga、Jian Yang、Yiding Zhang、Akiko Hatori、Katsushi Kumata、Jing Yang、Neil Vasdev、Yunfei Du、Chongzhao Ran、Ming-Rong Zhang、Steven H. Liang

  DOI：10.1021/acs.jmedchem.7b00432

  日期：2017.6.22

  A suitable TSPO PET ligand may visualize and quantify neuroinflammation in a living brain. Herein we report a F-18-ligand, [F-18]2 ([F-18]FDPA), is radiolabeled in high yield and high specific activity based on our spirocyclic iodonium ylide (SCIDY) strategy. [F-18]2. demonstrated saturable specific binding to TSPO, substantially elevated brain uptake, and slow washout of bound PET signal in the preclinical models of brain neuroinflammation (cerebral ischemia and Alzheimer's disease).