3-(2-fluorophenyl)oxazolidin-2-one

• 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: 3-(2-fluorophenyl)oxazolidin-2-one
• 英文别名: 3-(2-Fluorophenyl)-1,3-oxazolidin-2-one
• 化学式: C₉H₈FNO₂
• 分子量: 181.166
• InChiKey: BFVDQSUGDGOQPA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-(2-fluorophenyl)oxazolidin-2-one 在 potassium hydroxide 作用下， 以 乙醇 为溶剂， 生成 2-(2-fluorophenylamino)ethanol
  参考文献：
  名称：

  Bis-aryl Urea Derivatives as Potent and Selective LIM Kinase (Limk) Inhibitors

  摘要：

  The discovery/optimization of bis-aryl ureas as Limk inhibitors to obtain high potency and selectivity and appropriate pharmacokinetic properties through systematic SAR studies is reported. Docking studies supported the observed SAR. Optimized Limk inhibitors had high biochemical potency (IC50 < 25 nM), excellent selectivity against ROCK and JNK kinases (>400-fold), potent inhibition of cofilin phosphorylation in A7r5, PC-3, and CEM-SS T cells (IC50 < 1 mu M), and good in vitro and in vivo pharmacokinetic properties. In the profiling against a panel of 61 kinases, compound 18b at 1 mu M inhibited only Limk1 and STK16 with >= 80% inhibition. Compounds 18b and 18f were highly efficient in inhibiting cell-invasion/migration in PC-3 cells. In addition, compound 18w was demonstrated to be effective on reducing intraocular pressure (IOP) on rat eyes. Taken together, these data demonstrated that we had developed a novel class of bis-aryl urea derived potent and selective Limk inhibitors.

  DOI：

  10.1021/jm501680m
• 作为产物：
  描述：

  2-唑烷酮 、 2-氟碘苯 在 potassium phosphate 、 copper(l) iodide 、 (+/-)-trans-cyclohexanediamine 作用下， 以 1,4-二氧六环 为溶剂， 反应 3.5h， 以91%的产率得到3-(2-fluorophenyl)oxazolidin-2-one
  参考文献：
  名称：

  Copper-catalyzed N-Arylation of 2-Oxazolidinones. An Expeditious Route to Toloxatone

  摘要：

  3-Aryl-2-oxazolidinones are obtained in excellent yields through the copper-catalyzed N-arylation of 2-oxazolidinones with a variety of aryl iodides. With aryl halides containing both iodo and bromo substituents, a high C-I/C-Br selectivity can be achieved. The procedure has been successfully applied to the preparation of a key intermediate in the synthesis of linezolid and to develop an expeditious route to toloxatone.

  DOI：

  10.3987/com-03-s7

文献信息

• A One-Pot Synthesis of <i>N</i> -Aryl-2-Oxazolidinones and Cyclic Urethanes by the Lewis Base Catalyzed Fixation of Carbon Dioxide into Anilines and Bromoalkanes
  作者：Teemu Niemi、Jesus E. Perea-Buceta、Israel Fernández、Otto-Matti Hiltunen、Vili Salo、Sari Rautiainen、Minna T. Räisänen、Timo Repo

  DOI：10.1002/chem.201602338

  日期：2016.7.18

  catalytic amounts of an organosuperbase such as Barton's base enables this transformation to proceed with high yields and exquisite substrate functional‐group tolerance under ambient CO2 pressure and mild temperature. This report also provides the first proof‐of‐principle for the single‐operation synthesis of elusive seven‐membered ring cyclic urethanes.

  描述了通过将二氧化碳直接插入容易获得的苯胺和二溴代烷烃中的，具有药学意义的N-芳基-恶唑烷酮的多组分组装方法。添加催化量的有机超碱（如Barton碱）可使该转化在环境CO 2压力和温和温度下以高收率和出色的底物官能团耐受性进行。该报告还为难以捉摸的七元环环状氨基甲酸酯的单操作合成提供了第一个原理证明。
• Antimicrobial ortho-Fluorophenyl Oxazolidinones For Treatment of Bacterial Infections
  申请人：Gordeev Mikhail Fedorovich

  公开号：US20090048305A1

  公开（公告）日：2009-02-19

  The present invention provides certain ortho-fluorophenyl oxazolidinones of the following formula I: or pharmaceutically acceptable salts or prodrugs thereof that are antibacterial agents, pharmaceutical compositions containing them, methods for their use, and methods for preparing these compounds.

  本发明提供了以下结构式I的某些邻氟苯基噁唑啉酮化合物，或其药用可接受的盐或前药，这些化合物是抗菌剂，包含它们的药物组合物，以及使用这些化合物的方法和制备这些化合物的方法。
• Methods and Processes For Syntheses and Manufacture of Antimicrobial 1(Ortho-Fluorophenyl)dihydropyridones
  申请人：Wang Qiang

  公开号：US20100204477A1

  公开（公告）日：2010-08-12

  Provided herein are methods and processes for synthesis and manufacture of compounds of formula I: or its crystal forms, pharmaceutical acceptable salts, prodrugs, hydrates, or solvates thereof.

  本文提供了一种合成和制造化合物I的方法和过程：或其晶体形式、药用可接受盐、前药、水合物或溶剂化合物。
• [EN] ANTIMICROBIAL ORTHO-FLUOROPHENYL OXAZOLIDINONES FOR TREATMENT OF BACTERIAL INFECTIONS<br/>[FR] ORTHOFLUOROPHÉNYLE OXAZOLIDINONES ANTIMICROBIENNES POUR LE TRAITEMENT D'INFECTIONS BACTÉRIENNES
  申请人：MICURX PHARMACEUTICALS INC

  公开号：WO2009020616A1

  公开（公告）日：2009-02-12

  The present invention provides certain ortΛø-fluorophenyl oxazolidinones of the following formula ( I ): or pharmaceutically acceptable salts or prodrugs thereof that are antibacterial agents, pharmaceutical compositions containing them, methods for their use, and methods for preparing these compounds.

  本发明提供以下式子（I）的某些取代为氟代苯基的噁唑烷酮或其药学上可接受的盐或前药，它们是抗菌剂，以及含有它们的制药组合物、使用它们的方法和制备这些化合物的方法。
• [EN] OXAZOLIDINONES AND THEIR USE AS ANTIINFECTIVES<br/>[FR] OXAZOLIDINONES ET LEUR UTILISATION COMME ANTI-INFECTIEUX
  申请人：UPJOHN CO

  公开号：WO2001009107A1

  公开（公告）日：2001-02-08

  Compounds of formula (1) wherein: R6 is substituted thioacyl, aminocarbonyl, alkoxycarbonyl, aminothiocarbonyl, alkoxythiocarbonyl, alkylthio(carbonyl), or alkylthio(thiocarbonyl); R7 is aryl or heteroaryl; and R8-R9 are specified substituents; are useful in treating or preventing an infectious disorder in a human or other animal subject.

  公式（1）的化合物，其中：R6是取代基硫酰基，氨基甲酰基，烷氧羰基，氨基硫代甲酰基，烷氧硫代甲酰基，烷基硫（羰基）或烷基硫（硫代甲酰基）；R7是芳基或杂环芳基；R8-R9是指定的取代基；用于治疗或预防人类或其他动物主体的传染性疾病。