N-acetylfluvoxamine

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N-acetylfluvoxamine
• 英文别名: N-acetyl fluvoxamine；N-[2-[(E)-[5-methoxy-1-[4-(trifluoromethyl)phenyl]pentylidene]amino]oxyethyl]acetamide
• 化学式: C₁₇H₂₃F₃N₂O₃
• 分子量: 360.376
• InChiKey: YSZVMERYCWDAMG-CJLVFECKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  25
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  59.9
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  1-溴-4-甲氧基丁烷 在 copper(l) iodide 、 四甲基乙二胺 、 盐酸羟胺 、 碘 、 sodium acetate 、 silver fluoride 、 magnesium 、 三乙胺 、 potassium hydroxide 作用下， 以 乙醚 、 乙醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 55.0h， 生成 N-acetylfluvoxamine
  参考文献：
  名称：

  TCDA：芳烃和杂芳烃三氟甲基化的实用合成及其应用

  摘要：

  据报道，该试剂的实用合成为50 g规模的三氟甲硅烷基氯二氟乙酸酯（TCDA）。优化了用TCDA进行的三氟甲基化反应，该反应对于缺电子的，中性的，富含芳基/杂芳基的碘化物以及极好的官能团耐受性（如酯，酰胺，醛，羟基和羧酸。该试剂还用于三种医学上相关化合物的后期三氟甲基化。此外，该方法以10 g的规模合成了结构单元三氟甲基吡啶和一个药物相关分子Boc-氟西汀，证明了其在过程化学中的实际应用。

  DOI：

  10.1021/acs.oprd.6b00079

文献信息

• Selective serotonin reuptake inhibitors—A new modality for the treatment of lymphoma/leukaemia?
  作者：Christian Schuster、Nora Fernbach、Uwe Rix、Giulio Superti-Furga、Marion Holy、Michael Freissmuth、Harald H. Sitte、Veronika Sexl

  DOI：10.1016/j.bcp.2007.07.017

  日期：2007.11

  Selective serotonin reuptake inhibitors (SSRIs) have recently been reported to specifically kill malignant cells of B-lymphoid origin, i.e., cells derived from Burkitt lymphoma. Accordingly, SSRIs have been proposed as lead compounds in the development of new approaches to the treatment of lymphoma/leukaemia. Here we attempted to dissect the underlying signaling pathways by comparing susceptible and resistant cell lines. However, we found that all cell lines investigated underwent apoptotic cell death when exposed to SSRI concentrations exceeding 10 mu M regardless of whether the cell lines were derived from B- (e.g., Namalwa, Ramos, Daudi, RL7), T-lymphoid tumors (e.g., Molt-4, Jurkat, CCRF-CEM) or other sources. The structure-activity relationship readily distinguished the pro-apoptotic and growth inhibitory effect of SSRIs from their eponymous action (blockage of the serotonin transporter): acetylation of the SSRIs fluvoxamine and paroxetine abrogated the ability of these compounds to inhibit 5HT-uptake, but did not impair their cytotoxic action. Based on these data we conclude that (i) SSRIs inhibit growth of transformed cells, but that (h) this effect is neither specific for malignant cells nor specific for any particular cellular subset. (iii) The pro-apoptotic effect of SSRIs (at mu M concentrations) is unrelated to their principal pharmacological action, i.e., inhibition of serotonin uptake (at nM concentrations). SSRIs or improved versions thereof are therefore unlikely to represent useful lead compounds for inducing apoptosis in B-cell derived tumors: the underlying mechanism is not confined to any specific cell lineage. (C) 2007 Elsevier Inc. All rights reserved.
• TCDA: Practical Synthesis and Application in the Trifluoromethylation of Arenes and Heteroarenes
  作者：Jian Wang、Xiaomin Zhang、Zehong Wan、Feng Ren

  DOI：10.1021/acs.oprd.6b00079

  日期：2016.4.15

  A practical synthesis of the reagent trimethylsilyl chlorodifluoroacetate (TCDA) is reported on 50 g scale. The trifluoromethylation with TCDA was optimized, and the reaction shows very broad scope with respect to electron-deficient, -neutral, -rich aryl/heteroaryl iodides, as well as excellent functional group tolerability, such as ester, amide, aldehyde, hydroxyl, and carboxylic acid. The reagent

  据报道，该试剂的实用合成为50 g规模的三氟甲硅烷基氯二氟乙酸酯（TCDA）。优化了用TCDA进行的三氟甲基化反应，该反应对于缺电子的，中性的，富含芳基/杂芳基的碘化物以及极好的官能团耐受性（如酯，酰胺，醛，羟基和羧酸。该试剂还用于三种医学上相关化合物的后期三氟甲基化。此外，该方法以10 g的规模合成了结构单元三氟甲基吡啶和一个药物相关分子Boc-氟西汀，证明了其在过程化学中的实际应用。