N-[[(5S)-3-[3-fluoro-4-nitrile-phenyl]-2-oxo-5-oxazolidinyl]methyl] acetamide | 220010-58-2

• 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-[[(5S)-3-[3-fluoro-4-nitrile-phenyl]-2-oxo-5-oxazolidinyl]methyl] acetamide
• 英文别名: 5-(S)-acetamidomethyl-3-[4'-cyano-3'-fluorophenyl]oxazolidine-2-one；N-[[(5S)-3-(4-cyano-3-fluorophenyl)-2-oxo-1,3-oxazolidin-5-yl]methyl]acetamide
• CAS: 220010-58-2
• 化学式: C₁₃H₁₂FN₃O₃
• 分子量: 277.255
• InChiKey: GOGUMCLLWAFUAP-NSHDSACASA-N

物化性质

• 沸点：
  535.8±40.0 °C(Predicted)
• 密度：
  1.39±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  82.4
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N-[[(5S)-3-[3-fluoro-4-nitrile-phenyl]-2-oxo-5-oxazolidinyl]methyl] acetamide 在 吡啶 、 硫化氢 、 一水合肼 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 1.5h， 生成 (S)-N-[[3-[3-Fluoro-4-(5-fluoromethyl-1,3,4-thiadiazol-2-yl)phenyl]-2-oxo-5-oxazolidinyl]methyl]acetamide
  参考文献：
  名称：

  The synthesis and antibacterial activity of 1,3,4-Thiadiazole phenyl oxazolidinone analogues

  摘要：

  Replacement of the morpholine Gring of linezolid 1 with a 1,3,4-thiadiazolyl ring leads to oxazolidinone analogues 5 having potent antibacterial activity against both gram-positive and gram-negative organisms. Conversion of the C5 acetamide group to a thioacetamide further increases the potency of these compounds. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2003.07.018
• 作为产物：
  描述：

  氰化钾 、 (5S)-N-((3-(4-amino-3-fluorophenyl)-2-oxo-1,3-oxazolidin-5-yl)methyl)acetamide 在 盐酸 、 sodium nitrite 作用下， 以 水 、 乙酸乙酯 为溶剂， 反应 2.25h， 以72%的产率得到N-[[(5S)-3-[3-fluoro-4-nitrile-phenyl]-2-oxo-5-oxazolidinyl]methyl] acetamide
  参考文献：
  名称：

  The synthesis and antibacterial activity of 1,3,4-Thiadiazole phenyl oxazolidinone analogues

  摘要：

  Replacement of the morpholine Gring of linezolid 1 with a 1,3,4-thiadiazolyl ring leads to oxazolidinone analogues 5 having potent antibacterial activity against both gram-positive and gram-negative organisms. Conversion of the C5 acetamide group to a thioacetamide further increases the potency of these compounds. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2003.07.018

文献信息

• Oxazolidinone compounds and compositions, and methods of using the same
  申请人：Pharmacia & Upjohn Company

  公开号：US06441005B1

  公开（公告）日：2002-08-27

  Oxazolidinones and methods for their synthesis are provided. Further provided are methods of making biologically active oxazolidinones as well as pharmaceutically acceptable compositions comprising the oxazolidinones. Oxazolidinones as disclosed herein can be readily synthesized and used in a variety of applications including use as antimicrobial agents. In one embodiment, a variety of thioamidomethyloxazolidinones and methods for their synthesis and use are provided.

  提供了噁唑烷酮及其合成方法。此外，还提供了制备生物活性噁唑烷酮的方法，以及包含噁唑烷酮的药用合成物。本文所披露的噁唑烷酮可以很容易地合成并用于各种应用，包括用作抗微生物剂。在一个实施例中，提供了各种硫代氨基甲氧噁唑烷酮及其合成和使用方法。
• 1(2)H-tetrazol-5-yl-phenyl-oxazolidinones as antibacterial agents
  申请人：Ferrer Internacional, S.A.

  公开号：EP2072514A1

  公开（公告）日：2009-06-24

  The present invention provides a class of phenyl-oxazolidinones of formula (I): or a pharmaceutically acceptable salt thereof, wherein: R1 is a radical of formula (i) or formula (ii): methods of preparing such compounds, pharmaceutical compositions comprising one or more of such compounds, and the use thereof in the manufacture of a medicament which is used in the treatment of bacterial infections.

  本发明提供了一类苯基噁唑烷酮化合物，其化学式为(I)：或其药用可接受的盐，其中：R1为化学式(i)或化学式(ii)的基团；制备这类化合物的方法；包含一种或多种这类化合物的药物组合物；以及将其用于制造用于治疗细菌感染的药物的用途。
• Oxazolidinone compounds and methods of preparation and use thereof
  申请人：PHARMACIA & UPJOHN COMPANY

  公开号：US20020169191A1

  公开（公告）日：2002-11-14

  Oxazolidinones and methods for their synthesis are provided. Further provided are methods of making biologically active oxazolidinones as well as pharmaceutically acceptable compositions comprising the oxazolidinones. Oxazolidinones as disclosed herein can be readily synthesized and used in a variety of applications including use as antimicrobial agents. In one embodiment, a variety of thioamidomethyloxazolidinones and methods for their synthesis and use are provided.

  提供了氧杂环丙烷酮及其合成方法。还提供了制备生物活性氧杂环丙烷酮以及包含氧杂环丙烷酮的药学可接受组合物的方法。本文所披露的氧杂环丙烷酮可以很容易地合成并用于各种应用，包括用作抗菌剂。在一种实施例中，提供了各种硫酰胺甲基氧杂环丙烷酮及其合成和使用方法。
• Oxazalidinone compounds and methods of preparation and use thereof
  申请人：Pharmacia & Upjohn Company

  公开号：US06743811B2

  公开（公告）日：2004-06-01

  Oxazolidinones and methods for their synthesis are provided. Further provided are methods of making biologically active oxazolidinones as well as pharmaceutically acceptable compositions comprising the oxazolidinones. Oxazolidinones as disclosed herein can be readily synthesized and used in a variety of applications including use as antimicrobial agents. In one embodiment, a variety of thioamidomethyloxazolidinones and methods for their synthesis and use are provided.

  本发明提供了噁唑烷酮及其合成方法。还提供了制备生物活性噁唑烷酮的方法，以及包含噁唑烷酮的药学可接受组合物的方法。本发明所披露的噁唑烷酮可以很容易地合成，并可用于各种应用，包括用作抗微生物剂。在一种实施例中，提供了各种硫代酰胺甲基噁唑烷酮及其合成和使用方法。
• US6441005B1
  申请人：——

  公开号：US6441005B1

  公开（公告）日：2002-08-27