(+)-(1S,4S)-2-methyl-1-phenyl-1,4-dihydro-1,4-methano-2-benzazepine-3,5(2H)-dione | 165878-47-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯氮卓类
• 英文名称: (+)-(1S,4S)-2-methyl-1-phenyl-1,4-dihydro-1,4-methano-2-benzazepine-3,5(2H)-dione
• 英文别名: (1S,9S)-11-methyl-1-phenyl-11-azatricyclo[7.2.1.02,7]dodeca-2,4,6-triene-8,10-dione
• CAS: 165878-47-7
• 化学式: C₁₈H₁₅NO₂
• 分子量: 277.323
• InChiKey: XJIVRVKISIUQCJ-KSSFIOAISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  21
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  37.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (+)-(1S,4S)-2-methyl-1-phenyl-1,4-dihydro-1,4-methano-2-benzazepine-3,5(2H)-dione 在 sodium azide 、 硫酸 作用下， 反应 3.5h， 生成 CGP 48506 、 (-)-(3S,6S)-5-methyl-6-phenyl-2,3,5,6-tetrahydro-3,6-methano-2,5-benzodiazocine-1,4-dione
  参考文献：
  名称：

  5-Methyl-6-phenyl-1,3,5,6-tetrahydro-3,6-methano-1,5-benzodiazocine-2,4- dione (BA 41899): Representative of a Novel Class of Purely Calcium-Sensitizing Agents

  摘要：

  BA 41899 (5-methyl-6-phenyl-1,3,5,6-tetrahydro-3,6-methano-1,5-benzodiazocine-2,4-dione, 6) is a structurally novel 1,5-benzodiazocine derivative and represents the prototype of a hitherto unknown class of positive inotropic Ca2+-sensitizing agents. It is completely devoid of phosphodiesterase (PDE) III inhibitory activity or any other known inotropic mechanism. BA 41899 (6) exhibits a pharmacological in vitro profile comprising Ca2+-sensitizing, positive inotropic, and negative chronotropic effects. CGP 48506 ((+)-6), the (+)-enantiomer of BA 41899 (6), enantiospecifically carries Ca2+ sensitization by up to a full pCa unit and a corresponding positive inotropic effect. Conversely, the negative chronotropic action resides in the corresponding (-)-enantiomer, CGP 48508 ((-)-6). Ah the effects are exerted in the low micromolar range. The positive inotropic action of CGP 48506 ((+)-6) is associated with a decelerating effect on contraction and, more prominently, relaxation dynamics in isolated guinea pig atria. In contrast to Ca2+-sensitizing PDE inhibitors, CGP 48506 ((+)-6) does not increase maximum Ca2+-activated force in myocardial skinned fibers.

  DOI：

  10.1021/jm00015a017
• 作为产物：
  描述：

  1-phenyl-1,4-dihydro-1,4-methano-2-benzazepine-3,5(2H)-dione 在 potassium carbonate 、 臭氧 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 48.0h， 生成 (+)-(1S,4S)-2-methyl-1-phenyl-1,4-dihydro-1,4-methano-2-benzazepine-3,5(2H)-dione
  参考文献：
  名称：

  5-Methyl-6-phenyl-1,3,5,6-tetrahydro-3,6-methano-1,5-benzodiazocine-2,4- dione (BA 41899): Representative of a Novel Class of Purely Calcium-Sensitizing Agents

  摘要：

  BA 41899 (5-methyl-6-phenyl-1,3,5,6-tetrahydro-3,6-methano-1,5-benzodiazocine-2,4-dione, 6) is a structurally novel 1,5-benzodiazocine derivative and represents the prototype of a hitherto unknown class of positive inotropic Ca2+-sensitizing agents. It is completely devoid of phosphodiesterase (PDE) III inhibitory activity or any other known inotropic mechanism. BA 41899 (6) exhibits a pharmacological in vitro profile comprising Ca2+-sensitizing, positive inotropic, and negative chronotropic effects. CGP 48506 ((+)-6), the (+)-enantiomer of BA 41899 (6), enantiospecifically carries Ca2+ sensitization by up to a full pCa unit and a corresponding positive inotropic effect. Conversely, the negative chronotropic action resides in the corresponding (-)-enantiomer, CGP 48508 ((-)-6). Ah the effects are exerted in the low micromolar range. The positive inotropic action of CGP 48506 ((+)-6) is associated with a decelerating effect on contraction and, more prominently, relaxation dynamics in isolated guinea pig atria. In contrast to Ca2+-sensitizing PDE inhibitors, CGP 48506 ((+)-6) does not increase maximum Ca2+-activated force in myocardial skinned fibers.

  DOI：

  10.1021/jm00015a017

文献信息

• 5-Methyl-6-phenyl-1,3,5,6-tetrahydro-3,6-methano-1,5-benzodiazocine-2,4- dione (BA 41899): Representative of a Novel Class of Purely Calcium-Sensitizing Agents
  作者：Peter Herold、Joachim W. Herzig、Paul Wenk、Thomas Leutert、Paul Zbinden、Walter Fuhrer、Stefan Stutz、Karl Schenker、Max Meier、Greti Rihs

  DOI：10.1021/jm00015a017

  日期：1995.7

  BA 41899 (5-methyl-6-phenyl-1,3,5,6-tetrahydro-3,6-methano-1,5-benzodiazocine-2,4-dione, 6) is a structurally novel 1,5-benzodiazocine derivative and represents the prototype of a hitherto unknown class of positive inotropic Ca2+-sensitizing agents. It is completely devoid of phosphodiesterase (PDE) III inhibitory activity or any other known inotropic mechanism. BA 41899 (6) exhibits a pharmacological in vitro profile comprising Ca2+-sensitizing, positive inotropic, and negative chronotropic effects. CGP 48506 ((+)-6), the (+)-enantiomer of BA 41899 (6), enantiospecifically carries Ca2+ sensitization by up to a full pCa unit and a corresponding positive inotropic effect. Conversely, the negative chronotropic action resides in the corresponding (-)-enantiomer, CGP 48508 ((-)-6). Ah the effects are exerted in the low micromolar range. The positive inotropic action of CGP 48506 ((+)-6) is associated with a decelerating effect on contraction and, more prominently, relaxation dynamics in isolated guinea pig atria. In contrast to Ca2+-sensitizing PDE inhibitors, CGP 48506 ((+)-6) does not increase maximum Ca2+-activated force in myocardial skinned fibers.