tert-butyl (S)-7-bromo-9-oxo-11,12,13,13a-tetrahydro-9H-imidazo[1,5-a]pyrrolo[2,1-c][1,4]benzodiazepine-1-carboxylate | 84378-78-9

• 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: tert-butyl (S)-7-bromo-9-oxo-11,12,13,13a-tetrahydro-9H-imidazo[1,5-a]pyrrolo[2,1-c][1,4]benzodiazepine-1-carboxylate
• 英文别名: tert-butyl (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: 84378-78-9
• 化学式: C₁₉H₂₀BrN₃O₃
• 分子量: 418.29
• InChiKey: GTRFGCMGMHCDPF-AWEZNQCLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  26
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.42
• 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：

  tert-butyl (S)-7-bromo-9-oxo-11,12,13,13a-tetrahydro-9H-imidazo[1,5-a]pyrrolo[2,1-c][1,4]benzodiazepine-1-carboxylate 在 二乙酰二(三苯基膦)钯 TEA 、 四丁基氟化铵 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 反应 20.17h， 生成 tert-butyl (S)-7-ethynyl-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 acetate 、 sodium hydride 、 溶剂黄146 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 0.83h， 生成 tert-butyl (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

文献信息

• 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.