7-bromo-9-oxo-11,12,13,13a-tetrahydro-9H-imidazo[1,5-a]pyrrolo[2,1-c][1,4]benzodiazepine-1-carboxylic acid | 848034-23-1

• 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: 7-bromo-9-oxo-11,12,13,13a-tetrahydro-9H-imidazo[1,5-a]pyrrolo[2,1-c][1,4]benzodiazepine-1-carboxylic acid
• 英文别名: (7S)-15-bromo-12-oxo-2,4,11-triazatetracyclo[11.4.0.02,6.07,11]heptadeca-1(17),3,5,13,15-pentaene-5-carboxylic acid
• CAS: 848034-23-1
• 化学式: C₁₅H₁₂BrN₃O₃
• 分子量: 362.183
• InChiKey: RADJHDDVZSDJHP-NSHDSACASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  22
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  75.4
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  7-bromo-9-oxo-11,12,13,13a-tetrahydro-9H-imidazo[1,5-a]pyrrolo[2,1-c][1,4]benzodiazepine-1-carboxylic acid 在 四(三苯基膦)钯 N,N'-羰基二咪唑 作用下， 以 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 12.0h， 生成 2,2,2-trifluoroethyl (S)-7-(2-furyl)-9-oxo-11,12,13,13a-tetrahydro-9H-imidazo[1,5-a]pyrrolo[2,1-c][1,4]benzodiazepine-1-carboxylate
  参考文献：
  名称：

  Development of Selective Ligands for Benzodiazepine Receptor Subtypes by Manipulating the Substituents at Positions 3- and 7- of Optically Active BzR Ligands

  摘要：

  Two series of analogs of the optically active alpha5 subtype selective imidazobenzodiazepine 20 have been prepared. The framework constrained analogs were synthesized by variation of the C (3) ethyl ester function 20 to either t-butyl 7 or 2, 2, 2-trifluoroethyl 14. In both cases receptor binding was decreased; as well as alpha5 selectivity. In the second series the 7-acetylenyl function in 14 was varied over the range vinyl, 2-furyl, 2-thienyl and 2-phenyl. Again receptor binding was maintained in most cases; however, alpha5 selectivity was not increased. The significance of this in regard to occupation of lipophilic regions L-Di vs L-2 in the pharmacophore/receptor model of the BzR is discussed.

  DOI：

  10.1007/s00044-004-0033-7
• 作为产物：
  描述：

  (11aS)-7-bromo-2,3-dihydro-1H-benzo[e]pyrrolo[1,2-a][1,4]-diazepine-5,11-(10H,11aH)-dione 在 sodium hydroxide 、 sodium hydride 、 氯磷酸二乙酯 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 生成 7-bromo-9-oxo-11,12,13,13a-tetrahydro-9H-imidazo[1,5-a]pyrrolo[2,1-c][1,4]benzodiazepine-1-carboxylic acid
  参考文献：
  名称：

  Development of Selective Ligands for Benzodiazepine Receptor Subtypes by Manipulating the Substituents at Positions 3- and 7- of Optically Active BzR Ligands

  摘要：

  Two series of analogs of the optically active alpha5 subtype selective imidazobenzodiazepine 20 have been prepared. The framework constrained analogs were synthesized by variation of the C (3) ethyl ester function 20 to either t-butyl 7 or 2, 2, 2-trifluoroethyl 14. In both cases receptor binding was decreased; as well as alpha5 selectivity. In the second series the 7-acetylenyl function in 14 was varied over the range vinyl, 2-furyl, 2-thienyl and 2-phenyl. Again receptor binding was maintained in most cases; however, alpha5 selectivity was not increased. The significance of this in regard to occupation of lipophilic regions L-Di vs L-2 in the pharmacophore/receptor model of the BzR is discussed.

  DOI：

  10.1007/s00044-004-0033-7

文献信息

• GABAERGIC AGENTS TO TREAT MEMORY DEFICITS
  申请人：Cook M. James

  公开号：US20060258643A1

  公开（公告）日：2006-11-16

  The present invention provides molecules and methods for the prevention and/or treatment of memory deficit related conditions and/or enhancement of cognizance. In a preferred embodiment, the invention includes compounds, salts and prodrugs thereof for the prevention and/or treatment of these conditions.

  本发明提供了分子和方法，用于预防和/或治疗与记忆缺陷相关的疾病和/或提高认知能力。在一个首选实施例中，该发明包括化合物、盐和前药，用于预防和/或治疗这些疾病。
• GABAERGIC RECEPTOR SUBTYPE SELECTIVE LIGANDS AND THEIR USES
  申请人：Cook James M.

  公开号：US20120295892A1

  公开（公告）日：2012-11-22

  Described herein are α3 or α2 or α2/α3 GABAergic receptor subtype selective ligands, pharmaceutical compositions, and methods of use of such ligands and compositions in treatment of anxiety disorders, epilepsy and schizophrenia with reduced sedative and ataxic side effects. In embodiments, such as α3 or α2 or α2/α3 GABAergic receptor subtype selective ligands lack ester linkages and may be thus relatively insensitive to hydrolysis by esterases.

  本文描述了α3或α2或α2/α3 GABA能受体亚型选择性配体、药物组合物以及使用这些配体和组合物治疗焦虑症、癫痫和精神分裂症的方法，具有减少镇静和共济失调副作用。在某些实施例中，例如α3或α2或α2/α3 GABA能受体亚型选择性配体不含酯键，因此相对不容易被酯酶水解。
• US9006233B2
  申请人：——

  公开号：US9006233B2

  公开（公告）日：2015-04-14
• US9597342B2
  申请人：——

  公开号：US9597342B2

  公开（公告）日：2017-03-21