2-ethyl-7-fluoro-4-(3,4,5-trimethylpiperazin-1-yl)-10H-thieno[2,3-b][1,5]benzodiazepine | 82546-80-3

• 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: 2-ethyl-7-fluoro-4-(3,4,5-trimethylpiperazin-1-yl)-10H-thieno[2,3-b][1,5]benzodiazepine
• CAS: 82546-80-3
• 化学式: C₂₀H₂₅FN₄S
• 分子量: 372.51
• InChiKey: GBUCMOFKIFALMI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  26
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  59.1
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  2-ethyl-7-fluoro-5,10-dihydro-benzo[b]thieno[2,3-e][1,4]diazepin-4-one 、 1,2,6-trimethylpiperazine 在 四氯化钛 、 三乙胺 作用下， 以 various solvent(s) 为溶剂， 反应 3.0h， 以16%的产率得到2-ethyl-7-fluoro-4-(3,4,5-trimethylpiperazin-1-yl)-10H-thieno[2,3-b][1,5]benzodiazepine
  参考文献：
  名称：

  Effects of conformationally restricted 4-piperazinyl-10H-thienobenzodiazepine neuroleptics on central dopaminergic and cholinergic systems

  摘要：

  The levels of antidopaminergic and anticholinergic activities of neuroleptics, 4-piperazinyl-10H-thienobenzodiazepines, are modulated by imposing steric impedence to the piperazine ring. The optimum situation in favor of the anticholinergic action is reached in compound 5, 2,3-dimethyl-7-fluoro-4-(4-methyl-1-piperazinyl)-10H-thieno[2,3-b][1,5]benzodiazepine, where a maximum activity (equivalent to hyoscine), as measured by the [3H]QNB receptor binding assay, is obtained. The structure-activity relationships found highlight the importance of certain spatial dispositions of the distal piperazine nitrogen (electron lone pair) with respect to the tricyclic system. The evidence for molecular topography of these compounds is presented from X-ray, NMR, and other physical data. The conformational aspects for correspondence to the relevant receptors are discussed.

  DOI：

  10.1021/jm00352a007

文献信息

• Effects of conformationally restricted 4-piperazinyl-10H-thienobenzodiazepine neuroleptics on central dopaminergic and cholinergic systems
  作者：Jiban K. Chakrabarti、Terrence M. Hotten、Sarah E. Morgan、Ian A. Pullar、David M. Rackham、Francesca C. Risius、Susan Wedley、Michael O. Chaney、Noel D. Jones

  DOI：10.1021/jm00352a007

  日期：1982.10

  The levels of antidopaminergic and anticholinergic activities of neuroleptics, 4-piperazinyl-10H-thienobenzodiazepines, are modulated by imposing steric impedence to the piperazine ring. The optimum situation in favor of the anticholinergic action is reached in compound 5, 2,3-dimethyl-7-fluoro-4-(4-methyl-1-piperazinyl)-10H-thieno[2,3-b][1,5]benzodiazepine, where a maximum activity (equivalent to hyoscine), as measured by the [3H]QNB receptor binding assay, is obtained. The structure-activity relationships found highlight the importance of certain spatial dispositions of the distal piperazine nitrogen (electron lone pair) with respect to the tricyclic system. The evidence for molecular topography of these compounds is presented from X-ray, NMR, and other physical data. The conformational aspects for correspondence to the relevant receptors are discussed.