S-(2-bromoxyethyl) (3S,4R)-3-[(1,3-benzodioxol-5-yloxy)methyl]-4-(4-fluorophenyl)piperidine-1-carbothioate | 1170733-36-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: S-(2-bromoxyethyl) (3S,4R)-3-[(1,3-benzodioxol-5-yloxy)methyl]-4-(4-fluorophenyl)piperidine-1-carbothioate
• 英文别名: S-(2-bromoethyl) (3S,4R)-3-(1,3-benzodioxol-5-yloxymethyl)-4-(4-fluorophenyl)piperidine-1-carbothioate
• CAS: 1170733-36-4
• 化学式: C₂₂H₂₃BrFNO₄S
• 分子量: 496.397
• InChiKey: DNOGLRUBILISOU-LPHOPBHVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  30
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  73.3
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  S-(2-bromoxyethyl) (3S,4R)-3-[(1,3-benzodioxol-5-yloxy)methyl]-4-(4-fluorophenyl)piperidine-1-carbothioate 在 silver nitrate 作用下， 以 乙腈 为溶剂， 反应 6.0h， 以97%的产率得到S-(2-(nitrooxy)ethyl) (3S,4R)-3-((benzo[d][1,3]dioxol-5-yloxy)methyl)-4-(4-fluorophenyl)piperidine-1-carbothioate
  参考文献：
  名称：

  Chimeric Nitrate Esters and Use of the Same in a Treatment for Depression

  摘要：

  混合硝酸酯类化合物及其在治疗抑郁症中的应用被披露。这些混合硝酸酯类化合物也在治疗与衰老相关的抑郁症和共病中具有用途。

  公开号：

  US20090182011A1
• 作为产物：
  描述：

  盐酸帕罗西汀 在 三乙胺 、 三苯基膦 作用下， 以 二氯甲烷 为溶剂， 反应 9.25h， 生成 S-(2-bromoxyethyl) (3S,4R)-3-[(1,3-benzodioxol-5-yloxy)methyl]-4-(4-fluorophenyl)piperidine-1-carbothioate
  参考文献：
  名称：

  NO-SSRIs: Nitric Oxide Chimera Drugs Incorporating a Selective Serotonin Reuptake Inhibitor

  摘要：

  Hybrid nitrate drugs have been reported to provide NO bioactivity to ameliorate side effects or to provide ancillary therapeutic activity. Hybrid nitrate selective serotonin reuptake inhibitors (NO-SSRIs) were prepared to improve the therapeutic profile of this drug class. A synthetic strategy for use of a thiocarbamate linker was developed, which in the case of NO-fluoxetine facilitated hydrolysis to fluoxetine at pH 7.4 within 7 h. In cell culture, NO-SSRIs were weak inhibitors of the serotonin transporter; however, in the forced swimming task (FST) in rats, NO-fluoxetine demonstrated classical antidepressant activity. Comparison of NO-fluoxetine, with fluoxetine, and an NO-chimera nitrate developed for Alzheimer's disease (GT-1061) were made in the step through passive avoidance (STPA) test of learning and memory in rats treated with scopolamine as an amnesic agent. Fluoxetine was inactive, whereas NO-fluoxetine and GT-1061 both restored long-term memory. GT-1061 also produced antidepressant behavior in FST. These data support the potential for NO-SSRIs to overcome the lag in onset of therapeutic action and provide cotherapy of neuropathologies concomitant with depression.

  DOI：

  10.1021/ml2000033