N'-N-Diethyl-N'-[5-(2-fluoro-phenyl)-1-methyl-2,3-dihydro-1H-benzo[e][1,4]diazepin-2-ylmethyl]-methanediamine | 123903-91-3

• 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: N'-N-Diethyl-N'-[5-(2-fluoro-phenyl)-1-methyl-2,3-dihydro-1H-benzo[e][1,4]diazepin-2-ylmethyl]-methanediamine
• 英文别名: N',N'-diethyl-N-[[5-(2-fluorophenyl)-1-methyl-2,3-dihydro-1,4-benzodiazepin-2-yl]methyl]methanediamine
• CAS: 123903-91-3
• 化学式: C₂₂H₂₉FN₄
• 分子量: 368.497
• InChiKey: OEQQDJHWZBJNEH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  27
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  30.9
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  N,N-diethylethylenediamine 、 3-chloro-1-methyl-6-(2'-fluorophenyl)-1,2,3,4-tetrahydro-1,5-benzodiazocine 在 potassium carbonate 、 sodium iodide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 72.0h， 以92%的产率得到N'-N-Diethyl-N'-[5-(2-fluoro-phenyl)-1-methyl-2,3-dihydro-1H-benzo[e][1,4]diazepin-2-ylmethyl]-methanediamine
  参考文献：
  名称：

  Cholecystokinin-A receptor ligands based on the .kappa.-opioid agonist tifluadom

  摘要：

  Tifluadom, a kappa-opioid agonist and cholecystokinin-A (CCK-A) receptor antagonist, was utilized as a model to prepare a series of 2-(aminomethyl)- and 3-(aminomethyl)-1,4-benzodiazepines. These compounds were tested in vitro as inhibitors of the binding of [125I]CCK to rat pancreas and guinea pig brain receptors. All compounds with IC50's less than 100 microM proved to have greater affinity for the CCK-A receptor, with the most potent analogue, 6e, having an IC50 of 0.16 microM. The benzodiazepines described in this study are simultaneously CCK-A and opioid receptor ligands. The ramification of this dichotomy on current concepts of peptide hormone action are discussed. These results further demonstrate the versatility of the benzodiazepine core structure for designing nonpeptide ligands for peptide receptors and the ability to fine-tune the receptor interactions of these benzodiazepines by appropriate structure modifications.

  DOI：

  10.1021/jm00163a069

文献信息

• Cholecystokinin-A receptor ligands based on the .kappa.-opioid agonist tifluadom
  作者：Mark G. Bock、Robert M. DiPardo、Ben E. Evans、Kenneth E. Rittle、Willie L. Whitter、Daniel F. Veber、Roger M. Freidinger、Raymond S. L. Chang、T. B. Chen、Victor J. Lotti

  DOI：10.1021/jm00163a069

  日期：1990.1

  Tifluadom, a kappa-opioid agonist and cholecystokinin-A (CCK-A) receptor antagonist, was utilized as a model to prepare a series of 2-(aminomethyl)- and 3-(aminomethyl)-1,4-benzodiazepines. These compounds were tested in vitro as inhibitors of the binding of [125I]CCK to rat pancreas and guinea pig brain receptors. All compounds with IC50's less than 100 microM proved to have greater affinity for the CCK-A receptor, with the most potent analogue, 6e, having an IC50 of 0.16 microM. The benzodiazepines described in this study are simultaneously CCK-A and opioid receptor ligands. The ramification of this dichotomy on current concepts of peptide hormone action are discussed. These results further demonstrate the versatility of the benzodiazepine core structure for designing nonpeptide ligands for peptide receptors and the ability to fine-tune the receptor interactions of these benzodiazepines by appropriate structure modifications.