(R)-6-(2-fluorophenyl)-4-(1H-indol-3-ylmethyl)-4H-<1,2,4>triazolo<4,3-a><1,4>benzodiazepine | 103195-59-1

• 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: (R)-6-(2-fluorophenyl)-4-(1H-indol-3-ylmethyl)-4H-<1,2,4>triazolo<4,3-a><1,4>benzodiazepine
• 英文别名: 6-(2-Fluorophenyl)-4(R)-4-(3'-indolyl)methyl-4H-s-triazolo[4,3-a]-1,4-benzodiazepine；(R)-6-(2-fluorophenyl)-4-(1H-indol-3-ylmethyl)-4H-[1,2,4]triazolo[4,3-a][1,4]benzodiazepine；(4R)-6-(2-fluorophenyl)-4-(1H-indol-3-ylmethyl)-4H-[1,2,4]triazolo[4,3-a][1,4]benzodiazepine
• CAS: 103195-59-1
• 化学式: C₂₅H₁₈FN₅
• 分子量: 407.45
• InChiKey: QVRCFYZPIZQPGS-JOCHJYFZSA-N

物化性质

• 沸点：
  651.1±65.0 °C(Predicted)
• 密度：
  1.37±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  31
• 可旋转键数：
  3
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  58.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N,N-二甲基氯烯亚胺 、 (R)-6-(2-fluorophenyl)-4-(1H-indol-3-ylmethyl)-4H-<1,2,4>triazolo<4,3-a><1,4>benzodiazepine 以 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 以35%的产率得到(R)-6-(2-fluorophenyl)-4-(1H-indol-3-ylmethyl)-N,N-dimethyl-4H-<1,2,4>triazolo<4,3-a><1,4>benzodiazepine-1-methanamide
  参考文献：
  名称：

  Cholecystokinin antagonists. Synthesis and biological evaluation of 4-substituted 4H-[1,2,4]triazolo[4,3-a][1,4]benzodiazepines

  摘要：

  A series of 4-substituted 4H-[1,2,4]triazolo[4,3-a][1,4]benzodiazepines was prepared by standard methodology. These compounds were tested in vitro as antagonists of the binding of [125I]cholecystokinin (CCK) to rat pancreas and guinea pig brain receptors and of the binding of [125I]gastrin to guinea pig gastric glands. All compounds proved to have greater affinity for the peripheral CCK receptor with some analogues having IC50's in the subnanomolar range. In vivo activity of selected compounds in mice is presented and the structure/activity profile of this class of benzodiazepines as CCK antagonists is discussed.

  DOI：

  10.1021/jm00396a028
• 作为产物：
  描述：

  2H-1,4-苯并二氮卓-2-酮,5-(2-氟苯基)-1,3-二氢-3-(1H-吲哚-3-基甲基)-,(3R)- 在 劳森试剂 、 硫酸 、 肼 作用下， 以 甲醇 、 乙醇 、 甲苯 为溶剂， 反应 14.0h， 生成 (R)-6-(2-fluorophenyl)-4-(1H-indol-3-ylmethyl)-4H-<1,2,4>triazolo<4,3-a><1,4>benzodiazepine
  参考文献：
  名称：

  Cholecystokinin antagonists. Synthesis and biological evaluation of 4-substituted 4H-[1,2,4]triazolo[4,3-a][1,4]benzodiazepines

  摘要：

  A series of 4-substituted 4H-[1,2,4]triazolo[4,3-a][1,4]benzodiazepines was prepared by standard methodology. These compounds were tested in vitro as antagonists of the binding of [125I]cholecystokinin (CCK) to rat pancreas and guinea pig brain receptors and of the binding of [125I]gastrin to guinea pig gastric glands. All compounds proved to have greater affinity for the peripheral CCK receptor with some analogues having IC50's in the subnanomolar range. In vivo activity of selected compounds in mice is presented and the structure/activity profile of this class of benzodiazepines as CCK antagonists is discussed.

  DOI：

  10.1021/jm00396a028

文献信息

• BOCK, MARK G.;DIPARDO, ROBERT M.;EVANS, BEN E.;RITTLE, KENNETH E.;VEBER, +, J. MED. CHEM., 31,(1988) N 1, 176-181
  作者：BOCK, MARK G.、DIPARDO, ROBERT M.、EVANS, BEN E.、RITTLE, KENNETH E.、VEBER, +

  DOI：——

  日期：——
• Cholecystokinin antagonists. Synthesis and biological evaluation of 4-substituted 4H-[1,2,4]triazolo[4,3-a][1,4]benzodiazepines
  作者：Mark G. Bock、Robert M. DiPardo、Ben E. Evans、Kenneth E. Rittle、Daniel F. Veber、Roger M. Freidinger、Raymond S. L. Chang、Victor J. Lotti

  DOI：10.1021/jm00396a028

  日期：1988.1

  A series of 4-substituted 4H-[1,2,4]triazolo[4,3-a][1,4]benzodiazepines was prepared by standard methodology. These compounds were tested in vitro as antagonists of the binding of [125I]cholecystokinin (CCK) to rat pancreas and guinea pig brain receptors and of the binding of [125I]gastrin to guinea pig gastric glands. All compounds proved to have greater affinity for the peripheral CCK receptor with some analogues having IC50's in the subnanomolar range. In vivo activity of selected compounds in mice is presented and the structure/activity profile of this class of benzodiazepines as CCK antagonists is discussed.