5-(azidomethyl)-3-p-tolyloxazolidin-2-one | 1071789-16-6

• 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: 5-(azidomethyl)-3-p-tolyloxazolidin-2-one
• 英文别名: 5-(Azidomethyl)-3-(4-methylphenyl)-1,3-oxazolidin-2-one
• CAS: 1071789-16-6
• 化学式: C₁₁H₁₂N₄O₂
• 分子量: 232.242
• InChiKey: WANFQRMJAOFXNX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  43.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-癸炔 、 5-(azidomethyl)-3-p-tolyloxazolidin-2-one 在 copper(II) sulfate 、 sodium ascorbate 作用下， 以 水 、 叔丁醇 为溶剂， 以100%的产率得到5-((4-octyl-1H-1,2,3-triazol-1-yl)methyl)-3-p-tolyloxazolidin-2-one
  参考文献：
  名称：

  Synthesis of triazole-oxazolidinones via a one-pot reaction and evaluation of their antimicrobial activity

  摘要：

  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.

  DOI：

  10.1016/j.bmcl.2008.07.087
• 作为产物：
  描述：

  5-(bromomethyl)-3-p-tolyloxazolidin-2-one 在 sodium azide 、 四丁基碘化铵 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.5h， 以52%的产率得到5-(azidomethyl)-3-p-tolyloxazolidin-2-one
  参考文献：
  名称：

  Synthesis of triazole-oxazolidinones via a one-pot reaction and evaluation of their antimicrobial activity

  摘要：

  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.

  DOI：

  10.1016/j.bmcl.2008.07.087

文献信息

• OXAZOLIDINONE DERIVATIVE HAVING FUSED RING
  申请人：Katoh Issei

  公开号：US20110098471A1

  公开（公告）日：2011-04-28

  The present invention provides a novel antimicrobial drug comprising an oxazolidinone derivative of the formula (I): or a pharmaceutically acceptable salt or solvate thereof; wherein ring A is ring B is a benzene ring optionally substituted with lower alkyl; ring C is an optionally substituted six-membered heterocycle containing at least one nitrogen atom and one to three double bond(s) in the ling wherein the atom at the point of attachment to ring B is a carbon atom; ring D is an optionally substituted five-membered ring containing one or two double bond(s) in the ring; A 1 and A 2 are independently nitrogen or carbon; m is 0 or 1; R represents H, —NHC(═O)R A , —NHC(═S)R A , —NH-het 1 , —O-het 1 , —S-het 1 , —S(═O)-het 1 , —S(═O) 2 -het 1 , het 2 , —CONHR A , —OH, lower alkyl, lower alkoxy or lower alkenyl; and het 1 and het 2 are independently a heterocyclic group; with the proviso that the fused ring C-D is not

  本发明提供了一种新型抗菌药物，包括式(I)的噁唑烷酮衍生物： 或其药学上可接受的盐或溶剂；其中环A是 环B是一个苯环，可选择地取代为较低的烷基；环C是一个可选择地取代的含有至少一个氮原子和一个到三个双键的六元杂环，在连接到环B的点的原子是一个碳原子；环D是一个可选择地取代的含有一个或两个双键的五元环；A 1 和A 2 独立地是氮或碳；m为0或1；R代表H，—NHC(═O)R A ，—NHC(═S)R A ，—NH-het 1 ，—O-het 1 ，—S-het 1 ，—S(═O)-het 1 ，—S(═O) 2 -het 1 ，het 2 ，—CONHR A ，—OH，较低的烷基，较低的烷氧基或较低的烯基；和het 1 和het 2 独立地是一个杂环基团；但附带条件是融合的环C-D不是
• US8575337B2
  申请人：——

  公开号：US8575337B2

  公开（公告）日：2013-11-05
• 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.