2-methylpropoxycarbonyl 2-[6-(4-chlorophenyl)-5-oxo-7H-pyrrolo[3,4-b]pyridin-7-yl]acetate | 1026840-77-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯并吡啶类
• 英文名称: 2-methylpropoxycarbonyl 2-[6-(4-chlorophenyl)-5-oxo-7H-pyrrolo[3,4-b]pyridin-7-yl]acetate
• CAS: 1026840-77-6
• 化学式: C₂₀H₁₉ClN₂O₅
• 分子量: 402.834
• InChiKey: TVNQQJYSKUVPOT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  28
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  85.8
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  二已胺 、 2-methylpropoxycarbonyl 2-[6-(4-chlorophenyl)-5-oxo-7H-pyrrolo[3,4-b]pyridin-7-yl]acetate 以 四氢呋喃 为溶剂， 反应 1.0h， 生成 2-[6-(4-chlorophenyl)-5-oxo-7H-pyrrolo[3,4-b]pyridin-7-yl]-N,N-dihexylacetamide
  参考文献：
  名称：

  Molecular Basis of Peripheral vs Central Benzodiazepine Receptor Selectivity in a New Class of Peripheral Benzodiazepine Receptor Ligands Related to Alpidem

  摘要：

  Alpidem (1), the anxiolytic imidazopyridine, has nanomolar binding affinity for both the central benzodiazepine receptor (CBR) and the peripheral benzodiazepine receptor (PER). A novel class of PER ligands related to alpidem has been designed by comparing the interaction models of alpidem with PER and CBR. Several compounds in this class have shown high selectivity for PER vs CBR, and the selectivity has been discussed in terms of interaction models. The binding behavior of the three selected compounds was extensively studied by competition and saturation assays, and the results suggest that they are capable of recognizing two sites labeled by [H-3]PK11195. The molecular structure of one of the most active compounds (4e) has been determined by X-ray diffraction and compared with that of alpidem. Molecular modeling studies suggest that the bioactive conformation of 4e is Likely to be very similar to the conformation found in the crystal.

  DOI：

  10.1021/jm960325j
• 作为产物：
  描述：

  ethyl 2-bromomethylpyridine-3-carboxylate 在 sodium hydroxide 、 sodium hydride 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 三乙胺 作用下， 以 四氢呋喃 、 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 75.33h， 生成 2-methylpropoxycarbonyl 2-[6-(4-chlorophenyl)-5-oxo-7H-pyrrolo[3,4-b]pyridin-7-yl]acetate
  参考文献：
  名称：

  Molecular Basis of Peripheral vs Central Benzodiazepine Receptor Selectivity in a New Class of Peripheral Benzodiazepine Receptor Ligands Related to Alpidem

  摘要：

  Alpidem (1), the anxiolytic imidazopyridine, has nanomolar binding affinity for both the central benzodiazepine receptor (CBR) and the peripheral benzodiazepine receptor (PER). A novel class of PER ligands related to alpidem has been designed by comparing the interaction models of alpidem with PER and CBR. Several compounds in this class have shown high selectivity for PER vs CBR, and the selectivity has been discussed in terms of interaction models. The binding behavior of the three selected compounds was extensively studied by competition and saturation assays, and the results suggest that they are capable of recognizing two sites labeled by [H-3]PK11195. The molecular structure of one of the most active compounds (4e) has been determined by X-ray diffraction and compared with that of alpidem. Molecular modeling studies suggest that the bioactive conformation of 4e is Likely to be very similar to the conformation found in the crystal.

  DOI：

  10.1021/jm960325j

文献信息

• Molecular Basis of Peripheral vs Central Benzodiazepine Receptor Selectivity in a New Class of Peripheral Benzodiazepine Receptor Ligands Related to Alpidem
  作者：Maurizio Anzini、Andrea Cappelli、Salvatore Vomero、Gianluca Giorgi、Thierry Langer、Giancarlo Bruni、Maria R. Romeo、Anthony S. Basile

  DOI：10.1021/jm960325j

  日期：1996.1.1

  Alpidem (1), the anxiolytic imidazopyridine, has nanomolar binding affinity for both the central benzodiazepine receptor (CBR) and the peripheral benzodiazepine receptor (PER). A novel class of PER ligands related to alpidem has been designed by comparing the interaction models of alpidem with PER and CBR. Several compounds in this class have shown high selectivity for PER vs CBR, and the selectivity has been discussed in terms of interaction models. The binding behavior of the three selected compounds was extensively studied by competition and saturation assays, and the results suggest that they are capable of recognizing two sites labeled by [H-3]PK11195. The molecular structure of one of the most active compounds (4e) has been determined by X-ray diffraction and compared with that of alpidem. Molecular modeling studies suggest that the bioactive conformation of 4e is Likely to be very similar to the conformation found in the crystal.