3-(5-(2-fluorophenyl)-1-methyl-2-oxo-2,3-dihydro-1H-benzo[e][1,4]diazepin-3-yl)propanoic acid | 1078723-94-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯二氮卓类
• 英文名称: 3-(5-(2-fluorophenyl)-1-methyl-2-oxo-2,3-dihydro-1H-benzo[e][1,4]diazepin-3-yl)propanoic acid
• 英文别名: 3-[(3S)-5-(2-fluorophenyl)-1-methyl-2-oxo-3H-1,4-benzodiazepin-3-yl]propanoic acid
• CAS: 1078723-94-0
• 化学式: C₁₉H₁₇FN₂O₃
• 分子量: 340.354
• InChiKey: UOZTZPGMBDUOEW-HNNXBMFYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  25
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  70
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-(5-(2-fluorophenyl)-1-methyl-2-oxo-2,3-dihydro-1H-benzo[e][1,4]diazepin-3-yl)propanoic acid 在 硫酸 、 potassium nitrate 作用下， 反应 4.0h， 生成 3-(5-(2-fluorophenyl)-1-methyl-7-nitro-2-oxo-2,3-dihydro-1H-benzo[e][1,4]diazepin-3-yl)propanoic acid
  参考文献：
  名称：

  Prevention of Drug-Induced Memory Impairment by Immunopharmacotherapy

  摘要：

  One approach to treating drug abuse uses antidrug antibodies to immunize subjects against the illicit substance rather than administering the CNS site of action. At present, passive vaccination therapeutics that target the specific CNS has recognized efficacy in treating certain gross symptoms of drug misuse, namely, motor activation, self-administration, and overdose. However, the potential for antibodies to prevent drug-induced changes involving finer cognitive processes, such as benzodiazepine-associated amnesia, remains unexplored. To address this concept, a flunitrazepam hapten was synthesized and employed in the generation of a panel of high affinity monoclonal antibodies. Anti-flunitrazepam mAb RCA3A3 (K-d.app = 200 nM) was tested in a mouse model of passive immunization and subsequent mole-equivalent challenge with flunitrazepam. Not only was flunitrazepam-induced sedation prevented but immunization also conferred protection to memory consolidation as assessed through contextual and cued fear conditioning paradigms. These results provide evidence that immunopharmacotherapeutic blockade of drug intoxication also preserves complex cognitive function.

  DOI：

  10.1021/jm800506v
• 作为产物：
  描述：

  3-(5-(2-fluorophenyl)-2-oxo-2,3-dihydro-1H-benzo[e][1,4]diazepin-3-yl)propanoic acid 、 碘甲烷 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 0.17h， 以64%的产率得到3-(5-(2-fluorophenyl)-1-methyl-2-oxo-2,3-dihydro-1H-benzo[e][1,4]diazepin-3-yl)propanoic acid
  参考文献：
  名称：

  Prevention of Drug-Induced Memory Impairment by Immunopharmacotherapy

  摘要：

  One approach to treating drug abuse uses antidrug antibodies to immunize subjects against the illicit substance rather than administering the CNS site of action. At present, passive vaccination therapeutics that target the specific CNS has recognized efficacy in treating certain gross symptoms of drug misuse, namely, motor activation, self-administration, and overdose. However, the potential for antibodies to prevent drug-induced changes involving finer cognitive processes, such as benzodiazepine-associated amnesia, remains unexplored. To address this concept, a flunitrazepam hapten was synthesized and employed in the generation of a panel of high affinity monoclonal antibodies. Anti-flunitrazepam mAb RCA3A3 (K-d.app = 200 nM) was tested in a mouse model of passive immunization and subsequent mole-equivalent challenge with flunitrazepam. Not only was flunitrazepam-induced sedation prevented but immunization also conferred protection to memory consolidation as assessed through contextual and cued fear conditioning paradigms. These results provide evidence that immunopharmacotherapeutic blockade of drug intoxication also preserves complex cognitive function.

  DOI：

  10.1021/jm800506v