(2R)-2-{[4-(trifluoromethoxy)phenoxy]methyl}oxirane | 1166991-37-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (2R)-2-{[4-(trifluoromethoxy)phenoxy]methyl}oxirane
• 英文别名: (2R)-2-[[4-(trifluoromethoxy)phenoxy]methyl]oxirane
• CAS: 1166991-37-2
• 化学式: C₁₀H₉F₃O₃
• 分子量: 234.175
• InChiKey: TZNVDWDKRCCSMR-VIFPVBQESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  31
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (2R)-2-{[4-(trifluoromethoxy)phenoxy]methyl}oxirane 在 copper(l) iodide 、 magnesium sulfate 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 2.17h， 生成
  参考文献：
  名称：

  A low toxic CRM1 degrader: Synthesis and anti-proliferation on MGC803 and HGC27

  摘要：

  Chromosome region maintenance 1 (CRM1) is the sole nuclear exporter of several tumor suppressor, a growth regulatory protein as an attractive cancer drug target. In the present work, a novel CRM1 degrader was discovered from newly synthesized alpha, beta-unsaturated-delta-lactone based on a natural product Goniothalamin. It induces apoptosis of both MGC803 and HGC27 cell lines via degrading CRM1. Selective inhibition was observed for the proliferation of gastric cancer cell lines MGC803, HGC27 comparing to Human Gastric Mucosal Epithelial Cell Line (GES1). For the first time, CRM1 inhibitor or degrader inducing apoptosis in gastric carcinoma was investigated. (C) 2020 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2020.112708
• 作为产物：
  描述：

  对三氟甲氧基苯酚 、 (R)-(+)-间硝基苯磺酸缩水甘油酯 在 cesium fluoride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 36.0h， 以79%的产率得到(2R)-2-{[4-(trifluoromethoxy)phenoxy]methyl}oxirane
  参考文献：
  名称：

  重新定位抗结核的6-硝基-2,3-二氢咪唑并[2,1- b ] [1,3]恶唑类药物用于被忽视的热带病：内脏利什曼病的临床前候选者的结构-活性研究

  摘要：

  6-硝基-2,3-二氢咪唑[2,1- b最初在临床试验用药前驱体前药（PA-824）的备用程序中研究了[] [1,3]恶唑衍生物的结核病。表型筛选针对动素体疾病的代表性实例出乎意料地导致了DNDI-VL-2098的鉴定为潜在的内脏利什曼病（VL）的同类药物候选者。然后进行了其他工作来描述其基本结构特征，目的是在不损害针对VL的活性的情况下提高其溶解度和安全性。尽管4-硝基咪唑部分是特别需要的，但对芳氧基侧链的一些修饰是很好的耐受性，例如，将连接的氧交换成氮（或哌嗪），联芳基延伸以及用吡啶取代苯环。几种较不亲脂的类似物显示出改善的水溶性，尽管对肝微粒体的稳定性变化很大，但特别是在低pH下。在评估小鼠急性模型后利什曼原虫多诺万尼感染中，一种苯基吡啶衍生物（37）脱颖而出，其功效超过了临床前的先导药物。

  DOI：

  10.1021/acs.jmedchem.5b01699

文献信息

• 5-HT1F antagonists
  申请人：ELI LILLY AND COMPANY

  公开号：EP0976746A1

  公开（公告）日：2000-02-02

  This invention provides 5-HT1f antagonists of Formula I: where AR1, AR2, R, and R' are as defined in the specification.

  本发明提供了式 I 的 5-HT1f 拮抗剂： 其中 AR1、AR2、R 和 R' 如说明书中所定义。
• Use of 5HT-1F receptor antagonists for treating anxiety disorders
  申请人：ELI LILLY AND COMPANY

  公开号：EP0976747A2

  公开（公告）日：2000-02-02

  The present invention provides a method for the treatment of prevention of anxiety disorders which comprises administering to a mammal in need of such treatment a serotonin 5-HT1F receptor antagonist.

  本发明提供了一种治疗和预防焦虑症的方法，该方法包括向需要治疗的哺乳动物施用5-羟色胺5-HT1F受体拮抗剂。
• Discovery, synthesis, and biological evaluation of piperidinol analogs with anti-tuberculosis activity
  作者：Dianqing Sun、Michael S. Scherman、Victoria Jones、Julian G. Hurdle、Lisa K. Woolhiser、Susan E. Knudson、Anne J. Lenaerts、Richard A. Slayden、Michael R. McNeil、Richard E. Lee

  DOI：10.1016/j.bmc.2009.04.005

  日期：2009.5

  Direct anti-tuberculosis screening of commercially available compound libraries identified a novel piperidinol with interesting anti-tuberculosis activity and drug like characteristics. To generate a structure activity relationship about this hit a 22 member optimization library was generated using parallel synthesis. Products of this library 1-((R)-3-(4-chlorophenoxy)-2-hydroxypropyl)-4-(4-chloro-3-(trifluoromethyl) phenyl) piperidin-4-ol and 1-((S)-3-(4-(trifluoromethyl) phenoxy)-2-hydroxypropyl)-4-(4-chloro-3-( trifluoromethyl) phenyl) piperidin-4-ol demonstrated good anti-tuberculosis activity. Unfortunately, side effects were observed upon in vivo anti-tuberculosis testing of these compounds precluding their further advancement, which may be in part due to the secondary pharmacology associated with the aryl piperidinol core. (C) 2009 Elsevier Ltd. All rights reserved.
• US6242450B1
  申请人：——

  公开号：US6242450B1

  公开（公告）日：2001-06-05
• [EN] TREATMENT OF ANXIETY DISORDERS<br/>[FR] TRAITEMENT DES TROUBLES ANXIEUX
  申请人：LILLY CO ELI

  公开号：WO2000006082A2

  公开（公告）日：2000-02-10

  The present invention provides a method for the treatment or prevention of anxiety disorders which comprises administering to a mammal in need of such treatment a serotonin 5-HT1F receptor antagonist.