N,N-diethyl-[3-amino-5-(4-chlorophenyl)pyrazol-4-yl]acetamide | 386298-16-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: N,N-diethyl-[3-amino-5-(4-chlorophenyl)pyrazol-4-yl]acetamide
• CAS: 386298-16-4
• 化学式: C₁₅H₁₉ClN₄O
• 分子量: 306.795
• InChiKey: WIMJXIZLGXIOKK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.72
• 重原子数：
  21.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  75.01
• 氢给体数：
  2.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  二乙酰乙酸乙酯 、 N,N-diethyl-[3-amino-5-(4-chlorophenyl)pyrazol-4-yl]acetamide 以 乙醇 为溶剂， 反应 4.0h， 以70%的产率得到
  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-diethyl-[3-cyano-4-(4-chlorophenyl)-4-oxo]butanamide 在 一水合肼 、 溶剂黄146 作用下， 以 乙醇 为溶剂， 反应 6.0h， 以38%的产率得到N,N-diethyl-[3-amino-5-(4-chlorophenyl)pyrazol-4-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