(R)-<3-<4-(methylthio)phenyl>-2-oxo-5-oxazolidinyl>methyl 4-methylbenzenesulfonate | 121373-24-8

• 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: (R)-<3-<4-(methylthio)phenyl>-2-oxo-5-oxazolidinyl>methyl 4-methylbenzenesulfonate
• 英文别名: (R)-{3-[4-(methylthio)phenyl]-2-oxo-5-oxazolidinyl}methyl 4-methylbenzenesulfonate
• CAS: 121373-24-8
• 化学式: C₁₈H₁₉NO₅S₂
• 分子量: 393.485
• InChiKey: LTVBETNNAYXRLQ-OAHLLOKOSA-N

物化性质

• 沸点：
  568.5±33.0 °C(Predicted)
• 密度：
  1.41±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.45
• 重原子数：
  26.0
• 可旋转键数：
  6.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  72.91
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  (R)-<3-<4-(methylthio)phenyl>-2-oxo-5-oxazolidinyl>methyl 4-methylbenzenesulfonate 在 1,3-丙二硫醇 、 sodium hydroxide 、 sodium azide 、 18-冠醚-6 、 三乙胺 、 间氯过氧苯甲酸 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 25.5h， 生成 N-[3-(4-甲基亚磺酰苯基)-2-氧代-1,3-恶唑烷-5-基甲基]乙酰胺
  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：

  (R)-<3-<4-(methylthio)phenyl>-2-oxo-5-oxazolidinyl>methyl butyrate 在 吡啶 、 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 2.0h， 生成 (R)-<3-<4-(methylthio)phenyl>-2-oxo-5-oxazolidinyl>methyl 4-methylbenzenesulfonate
  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

文献信息

• Aminomethyl oxooxazolidinyl benzenes useful as antibacterial agents
  申请人：E. I. Du Pont de Nemours and Company

  公开号：US04705799A1

  公开（公告）日：1987-11-10

  Novel aminomethyl oxooxazolidinyl benzene derivatives, including the sulfides, sulfoxides, sulfones and sulfonamides, such as (l)-N-[3-[4-(methylsulfinyl)phenyl]-2-oxooxazolidin-5-ylmethyl]acetamide, possess useful antibacterial activity.

  新型氨甲基氧噁唑啉基苯衍生物，包括硫醚、亚硫醚、磺酰和磺酰胺衍生物，如（l）-N-[3-[4-(甲基亚磺基)苯基]-2-氧噁唑啉-5-基甲基]乙酰胺，具有有用的抗菌活性。
• Glycidyl Tosylate is a Viable Starting Material for Oxazolidinone Antibacterials
  作者：Cho-Rom Kim、Soo-Y. Ko

  DOI：10.5012/bkcs.2011.32.12.4450

  日期：2011.12.20