1-[(7-Fluoro-benzo-1,4-dioxan-2-yl)-methyl]-4-(5-fluorobenzimidazol-2-on-1-yl)-piperidine | 107617-60-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并二恶烷
• 英文名称: 1-[(7-Fluoro-benzo-1,4-dioxan-2-yl)-methyl]-4-(5-fluorobenzimidazol-2-on-1-yl)-piperidine
• 英文别名: 6-fluoro-3-[1-[(6-fluoro-2,3-dihydro-1,4-benzodioxin-3-yl)methyl]piperidin-4-yl]-1H-benzimidazol-2-one
• CAS: 107617-60-7
• 化学式: C₂₁H₂₁F₂N₃O₃
• 分子量: 401.413
• InChiKey: IYSCZWNPAOVAEQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  29
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  54
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  (7-fluoro-2,3-dihydrobenzo [b][1,4]dioxin-2-yl)methanol 在 吡啶 、 三乙胺 、 potassium iodide 作用下， 以 二甲基亚砜 为溶剂， 反应 25.0h， 生成 1-[(7-Fluoro-benzo-1,4-dioxan-2-yl)-methyl]-4-(5-fluorobenzimidazol-2-on-1-yl)-piperidine
  参考文献：
  名称：

  Synthesis and neuroleptic activity of a series of 1-[1-(benzo-1,4-dioxan-2-ylmethyl)-4-piperidinyl]benzimidazolone derivatives

  摘要：

  A series of 1-[1-(benzo-1,4-dioxan-2-ylmethyl)-4-piperidinyl]benzimid azolones with various substituents in both aromatic rings have been synthesized and tested for neuroleptic activity (antiapomorphine effects and [3H]spiroperidol binding) as well as extrapyramidal effects (cataleptogenic effect). A strong dependence of activity on the 5-substituent in the benzimidazolone moiety could be demonstrated. Some compounds show a large split between the desired antiapomorphine and the undesired extrapyramidal effect. From these, 1-[1-(benzo-1,4-dioxan-2-ylmethyl)-4-piperidinyl]-5-chlor obenzimidazol-2-one hydrochloride (HR 723), 12, has been selected for further preclinical and toxicological profiling.

  DOI：

  10.1021/jm00388a012

文献信息

• HENNING R.; LATTRELL R.; GARHARDS H. J.; LEVEN M., J. MED. CHEM., 30,(1987) N 5, 814-819
  作者：HENNING R.、 LATTRELL R.、 GARHARDS H. J.、 LEVEN M.

  DOI：——

  日期：——
• N-Oxacyclyl-Alkylpiperidin-Derivate, Verfahren zu ihrer Herstellung, sie enthaltende pharmazeutische Präparate und deren Verwendung
  申请人：HOECHST AKTIENGESELLSCHAFT

  公开号：EP0068261B1

  公开（公告）日：1985-04-03
• US4470989A
  申请人：——

  公开号：US4470989A

  公开（公告）日：1984-09-11
• Synthesis and neuroleptic activity of a series of 1-[1-(benzo-1,4-dioxan-2-ylmethyl)-4-piperidinyl]benzimidazolone derivatives
  作者：Rainer Henning、Rudolf Lattrell、Hermann J. Gerhards、Margret Leven

  DOI：10.1021/jm00388a012

  日期：1987.5

  A series of 1-[1-(benzo-1,4-dioxan-2-ylmethyl)-4-piperidinyl]benzimid azolones with various substituents in both aromatic rings have been synthesized and tested for neuroleptic activity (antiapomorphine effects and [3H]spiroperidol binding) as well as extrapyramidal effects (cataleptogenic effect). A strong dependence of activity on the 5-substituent in the benzimidazolone moiety could be demonstrated. Some compounds show a large split between the desired antiapomorphine and the undesired extrapyramidal effect. From these, 1-[1-(benzo-1,4-dioxan-2-ylmethyl)-4-piperidinyl]-5-chlor obenzimidazol-2-one hydrochloride (HR 723), 12, has been selected for further preclinical and toxicological profiling.