ethyl 3-(4-bromobenzoyl)-2-[(2,4-dichlorophenyl)hydrazono]-pentanoate | 288104-78-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: ethyl 3-(4-bromobenzoyl)-2-[(2,4-dichlorophenyl)hydrazono]-pentanoate
• 英文别名: Ethyl 3-(4-bromobenzoyl)-2-[(2,4-dichlorophenyl)hydrazinylidene]pentanoate
• CAS: 288104-78-9
• 化学式: C₂₀H₁₉BrCl₂N₂O₃
• 分子量: 486.192
• InChiKey: BIDJKPGFEZITOM-UHFFFAOYSA-N

物化性质

• 沸点：
  559.6±60.0 °C(Predicted)
• 密度：
  1.44±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.5
• 重原子数：
  28
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  67.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  ethyl 3-(4-bromobenzoyl)-2-[(2,4-dichlorophenyl)hydrazono]-pentanoate 在 溶剂黄146 作用下， 反应 24.0h， 以1.35 g的产率得到5-(4-bromophenyl)-1-(2,4-dichlorophenyl)-4-ethyl-1H-pyrazole-3-carboxylic acid ethyl ester
  参考文献：
  名称：

  Discovery of 2-[5-(4-Chloro-phenyl)-1-(2,4-dichloro-phenyl)-4-ethyl-1H-pyrazol-3-yl]-1,5,5-trimethyl-1,5-dihydro-imidazol-4-thione (BPR-890) via an Active Metabolite. A Novel, Potent and Selective Cannabinoid-1 Receptor Inverse Agonist with High Antiobesity Efficacy in DIO Mice

  摘要：

  By using the active metabolite 5 as an initial template, further structural modifications led to the identification of the titled compound 24 (BPR-890) as a highly potent CB I inverse agonist possessing an excellent CB2/1 selectivity and remarkable in vivo efficacy in diet-induced obese mice with a minimum effective dose as low as 0.03 mg/kg (po qd) at the end of the 30-day chronic study. Current SAR studies along with those of many existing rimonabant-mimicking molecules imply that around the pyrazole C3-position, a rigid and deep binding pocket should exist for CB1 receptor. In addition, relative to the conventional carboxamide carbonyl, serving as a key hydrogen-bond acceptor during ligand-CB1 receptor interaction, the corresponding polarizable thione carbonyl might play a more critical role in stabilizing the Asp366-Lys192 salt bridge in the proposed CB1-receptor homology model and inducing significant selectivity for CB1R over CB2R.

  DOI：

  10.1021/jm900471u
• 作为产物：
  描述：

  ethyl 3-(4-Bromobenzoyl)-2-oxopentanoate 、 2,4-二氯苯肼盐酸盐 生成 ethyl 3-(4-bromobenzoyl)-2-[(2,4-dichlorophenyl)hydrazono]-pentanoate
  参考文献：
  名称：

  WO2008/102367

  摘要：

  公开号：