<3-(4-acetylphenyl)-2-oxo-5-oxazolidinyl>methyl azide | 96800-65-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: <3-(4-acetylphenyl)-2-oxo-5-oxazolidinyl>methyl azide
• 英文别名: 3-p-acetylphenyl-5-azidomethyl-1,3-oxazolidin-2-one；(l)-3-(4-acetylphenyl)-5-(azidomethyl)-2-oxazolidinone；3-(4-Acetylphenyl)-5-(azidomethyl)-1,3-oxazolidin-2-one
• CAS: 96800-65-6
• 化学式: C₁₂H₁₂N₄O₃
• 分子量: 260.252
• InChiKey: LRCJJYOMQSDMAQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  61
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  <3-(4-acetylphenyl)-2-oxo-5-oxazolidinyl>methyl azide 在 三甲氧基磷 作用下， 以 乙二醇二甲醚 为溶剂， 反应 1.5h， 以37%的产率得到5-(aminomethyl)-3-(4-acetylphenyl)-2-oxooxazolidine
  参考文献：
  名称：

  Antibacterials. Synthesis and structure-activity studies of 3-aryl-2-oxooxazolidines. 1. The B group

  摘要：

  The synthesis and structure/activity studies of the effect of varying the "B" group in a series of oxazolidinone antibacterials (I) are described. Two synthetic routes were used: (1) alkylation of aniline with glycidol followed by dialkyl carbonate heterocyclization to afford I (A = H, B = OH), whose arene ring was further elaborated by using electrophilic aromatic substitution methodology; (2) cycloaddition of substituted aryl isocyanates with epoxides to give A and B with a variety of values. I with B = OH or Br were converted to other "B" functionalities by using SN2 methodology. Antibacterial evaluation of compounds I with A = acetyl, isopropyl, methylthio, methylsulfinyl, methylsulfonyl, and sulfonamido and a variety of different "B" groups against Staphylococcus aureus and Enterococcus faecalis concluded that the compounds with B = aminoacyl, and particularly acetamido, were the most active of those examined in each A series, possessing MICs in the range of 0.5-4 micrograms/mL for the most active compounds described.

  DOI：

  10.1021/jm00128a003
• 作为产物：
  描述：

  5-azidomethyl-3-phenyl-1,3-oxazolidin-2-one 在 乙酸酐 作用下， 以 甲烷磺酸 为溶剂， 生成 <3-(4-acetylphenyl)-2-oxo-5-oxazolidinyl>methyl azide
  参考文献：
  名称：

  Aminomethyl oxooxazolidinyl benzenes useful as antibacterial agents

  摘要：

  新型氨甲基氧噁唑啉基苯衍生物，包括硫化物、亚硫酸盐、磺酰化物和磺酰胺，例如（l）-N-[3-[4-(甲基亚磺酰基)苯基]-2-氧噁唑啉-5-基甲基]乙酰胺，具有有用的抗菌活性。

  公开号：

  US04705799A1

文献信息

• Synthesis of Oxazolidinones by a Solid-Phase/Activation Cycloelimination (SP/ACE) Methodology
  作者：Peter ten Holte、Bart C. J. van Esseveldt、Lambertus Thijs、Binne Zwanenburg

  DOI：10.1002/1099-0690(200108)2001:15<2965::aid-ejoc2965>3.0.co;2-z

  日期：2001.8

  A versatile method for the solid-phase synthesis of oxazolidinones is described, An appropriate 1,2-diol is attached to immobilized sulfonyl chloride, resulting in the selective activation of one of the alcohol functions, The subsequent reaction of the other alcohol group with an isocyanate, followed by a base-promoted cycloelimination gives an oxazolidinone, By proper choice of isocyanates, functionalities can be introduced which are essential for antibiotic activity.
• Synthesis of triazole-oxazolidinones via a one-pot reaction and evaluation of their antimicrobial activity
  作者：Jeffrey A. Demaray、Jason E. Thuener、Matthew N. Dawson、Steven J. Sucheck

  DOI：10.1016/j.bmcl.2008.07.087

  日期：2008.9

  C-5-substituted triazole-oxazolidinones were synthesized using a bromide catalyzed cycloaddition between aryl isocyanates and epibromohydrin followed by a three-component Huisgen cycloaddition. The library of compounds was screened for antibacterial activity against Mycobacterium smegmatis ATCC 14468, Bacillus subtilis ATCC 6633, and Enterococcus faecalis ATCC 29212. Notably, the 3-(4-acetyl-phenyl)5-(1H-1,2,3-triazol-1-yl) methyl)-oxazolidin-2-one (18) showed an MIC of 1 mu g/mL against M. smegmatis ATCC 14468, fourfold lower than the MIC measured for isoniazid. Published by Elsevier Ltd.
• GREGORY, WALTER A.
  作者：GREGORY, WALTER A.

  DOI：——

  日期：——
• US4705799A
  申请人：——

  公开号：US4705799A

  公开（公告）日：1987-11-10
• Antibacterials. Synthesis and structure-activity studies of 3-aryl-2-oxooxazolidines. 1. The B group
  作者：Walter A. Gregory、David R. Brittelli、C. L. J. Wang、Mark A. Wuonola、Ronald J. McRipley、David C. Eustice、Virginia S. Eberly、Andrew M. Slee、Martin Forbes、P. T. Bartholomew

  DOI：10.1021/jm00128a003

  日期：1989.8

  The synthesis and structure/activity studies of the effect of varying the "B" group in a series of oxazolidinone antibacterials (I) are described. Two synthetic routes were used: (1) alkylation of aniline with glycidol followed by dialkyl carbonate heterocyclization to afford I (A = H, B = OH), whose arene ring was further elaborated by using electrophilic aromatic substitution methodology; (2) cycloaddition of substituted aryl isocyanates with epoxides to give A and B with a variety of values. I with B = OH or Br were converted to other "B" functionalities by using SN2 methodology. Antibacterial evaluation of compounds I with A = acetyl, isopropyl, methylthio, methylsulfinyl, methylsulfonyl, and sulfonamido and a variety of different "B" groups against Staphylococcus aureus and Enterococcus faecalis concluded that the compounds with B = aminoacyl, and particularly acetamido, were the most active of those examined in each A series, possessing MICs in the range of 0.5-4 micrograms/mL for the most active compounds described.