(S)-N-[[3-[3-Fluoro-4-[5-[(methylthio)methyl]-1,3,4-thiadiazol-2-yl]phenyl]-2-oxo-5-oxazolidinyl]methyl]acetamide | 220009-99-4

• 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: (S)-N-[[3-[3-Fluoro-4-[5-[(methylthio)methyl]-1,3,4-thiadiazol-2-yl]phenyl]-2-oxo-5-oxazolidinyl]methyl]acetamide
• 英文别名: N-[[(5S)-3-[3-fluoro-4-[5-(methylsulfanylmethyl)-1,3,4-thiadiazol-2-yl]phenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl]acetamide
• CAS: 220009-99-4
• 化学式: C₁₆H₁₇FN₄O₃S₂
• 分子量: 396.466
• InChiKey: QBJIFJLJOMLJSN-NSHDSACASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  26
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  138
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  (S)-N-[[3-[3-Fluoro-4-[5-[(methylthio)methyl]-1,3,4-thiadiazol-2-yl]phenyl]-2-oxo-5-oxazolidinyl]methyl]acetamide 在 劳森试剂 、 Oxone 作用下， 以 1,4-二氧六环 为溶剂， 生成 N-[[(5S)-3-[3-fluoro-4-[5-(methylsulfonylmethyl)-1,3,4-thiadiazol-2-yl]phenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl]ethanethioamide
  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：

  (5S)-N-((3-(4-amino-3-fluorophenyl)-2-oxo-1,3-oxazolidin-5-yl)methyl)acetamide 在 吡啶 、 盐酸 、 硫化氢 、 一水合肼 、 三乙胺 、 sodium nitrite 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 3.75h， 生成 (S)-N-[[3-[3-Fluoro-4-[5-[(methylthio)methyl]-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

文献信息

• US5977373A
  申请人：——

  公开号：US5977373A

  公开（公告）日：1999-11-02
• The synthesis and antibacterial activity of 1,3,4-Thiadiazole phenyl oxazolidinone analogues
  作者：Lisa M Thomasco、Robert C Gadwood、Elizabeth A Weaver、Jason M Ochoada、Charles W Ford、Gary E Zurenko、Judith C Hamel、Douglas Stapert、Judy K Moerman、Ronda D Schaadt、Betty H Yagi

  DOI：10.1016/j.bmcl.2003.07.018

  日期：2003.12

  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.