(S)-ethyl 7-bromo-11,12,13,13a-tetrahydro-9-oxo-9H-imidazo[1,5-a]pyrrolo[2,1-d][1,4]benzodiazepine-1-carboxylate | 188739-26-6

• 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: (S)-ethyl 7-bromo-11,12,13,13a-tetrahydro-9-oxo-9H-imidazo[1,5-a]pyrrolo[2,1-d][1,4]benzodiazepine-1-carboxylate
• 英文别名: ethyl (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-carboxylate
• CAS: 188739-26-6
• 化学式: C₁₇H₁₆BrN₃O₃
• 分子量: 390.236
• InChiKey: NUXNKKUXSDGYTN-ZDUSSCGKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  24
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  64.4
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (S)-ethyl 7-bromo-11,12,13,13a-tetrahydro-9-oxo-9H-imidazo[1,5-a]pyrrolo[2,1-d][1,4]benzodiazepine-1-carboxylate 在 sodium hydroxide 、 N,N'-羰基二咪唑 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 12.0h， 生成 2,2,2-trifluoroethyl (S)-7-bromo-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：

  (S)-(+)-2,3-二氢-1H-吡咯并[2,1-c][1,4]苯并二氮卓-5,11(10H,11aH)-二酮 在 溴 、 sodium hydride 、 氯磷酸二乙酯 作用下， 以 四氢呋喃 、 硫酸 、 溶剂黄146 、 N,N-二甲基甲酰胺 为溶剂， 生成 (S)-ethyl 7-bromo-11,12,13,13a-tetrahydro-9-oxo-9H-imidazo[1,5-a]pyrrolo[2,1-d][1,4]benzodiazepine-1-carboxylate
  参考文献：
  名称：

  Liu, Ruiyan; Zhang, Puwen; Gan, Tong, Medicinal Chemistry Research, 1997, vol. 7, # 1, p. 25 - 35

  摘要：

  DOI：

文献信息

• An Improved Process for the Synthesis of 4<i>H</i>-Imidazo[1,5-<i>a</i>][1,4]benzo­diazepines
  作者：Jie Yang、Yun Teng、Shamim Ara、Sundari Rallapalli、James Cook

  DOI：10.1055/s-0028-1083358

  日期：——

  The construction of CNS active imidazo[1,5-a][1,4]benzodiazepines has been improved in a one-pot annulation process. GABAA/Bz receptors - imidazo[1,5-a][1,4]benzodiazepines - ethyl isocyanoacetate - annulation

  CNS活性咪唑并[1,5- a ] [1,4]苯并二氮杂卓的结构已通过一锅法制得。 GABA A / Bz受体-咪唑并[1,5- a ] [1,4]苯并二氮杂卓-异氰基乙酸乙酯-环化
• 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。
• Liu, Ruiyan; Zhang, Puwen; Gan, Tong, Medicinal Chemistry Research, 1997, vol. 7, # 1, p. 25 - 35
  作者：Liu, Ruiyan、Zhang, Puwen、Gan, Tong、McKernan, Ruth M.、Cook, James M.

  DOI：——

  日期：——
• Development of Selective Ligands for Benzodiazepine Receptor Subtypes by Manipulating the Substituents at Positions 3- and 7- of Optically Active BzR Ligands
  作者：Xiaoyan Li、Jianming Yu、John R. Atack、James M. Cook

  DOI：10.1007/s00044-004-0033-7

  日期：2004.6

  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.