(R)-3-(4-(4-(2-(bicyclo[2.2.1]heptan-2-yl)acetyl)piperazin-1-yl)-3-fluorophenyl)-5-((4-methyl-1H-1,2,3-triazol-1-yl)methyl)oxazolidin-2-one | 1170679-29-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪烷类
• 英文名称: (R)-3-(4-(4-(2-(bicyclo[2.2.1]heptan-2-yl)acetyl)piperazin-1-yl)-3-fluorophenyl)-5-((4-methyl-1H-1,2,3-triazol-1-yl)methyl)oxazolidin-2-one
• 英文别名: (5R)-3-[4-[4-[2-(2-bicyclo[2.2.1]heptanyl)acetyl]piperazin-1-yl]-3-fluorophenyl]-5-[(4-methyltriazol-1-yl)methyl]-1,3-oxazolidin-2-one
• CAS: 1170679-29-4
• 化学式: C₂₆H₃₃FN₆O₃
• 分子量: 496.585
• InChiKey: MLKCEMFAEYMVSN-JJECGNGTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  36
• 可旋转键数：
  6
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  83.8
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  (R)-4-(2-fluoro-4-(5-((4-methyl-1H-1,2,3-triazol-1-yl)methyl)-2-oxooxazolidin-3-yl)phenyl)piperazin-1-ium 2,2,2-trifluoroacetate 、 2-降莰烷乙酸 在 1-羟基苯并三唑 、 N,N'-二环己基碳二亚胺 、 三乙胺 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 2.0h， 以52%的产率得到(R)-3-(4-(4-(2-(bicyclo[2.2.1]heptan-2-yl)acetyl)piperazin-1-yl)-3-fluorophenyl)-5-((4-methyl-1H-1,2,3-triazol-1-yl)methyl)oxazolidin-2-one
  参考文献：
  名称：

  Synthesis and antibacterial activity of novel 5-(4-methyl-1H-1,2,3-triazole) methyl oxazolidinones

  摘要：

  A series of 5-(4-methyl-1,2,3-triazole)methyl oxazolidinones were synthesized and tested for their antibacterial activity against a panel of Gram-positive and Gram-negative clinical isolates in comparison with linezolid and vancomycin. Most of the compounds demonstrated strong to moderate in vitro antibacterial activity against susceptible and resistant Gram-positive pathogenic bacteria. Antibacterial activity varied with substitutions at the phenyl C4 position with bulky alkylcarbonyl and alkoxycarbonyl substitutions on the piperazine N4 being detrimental to antibacterial activity. Whereas the presence of the 4-methyl-1,2,3-triazole moiety in the acyl-piperazine containing analogs resulted in increased protein binding, and decreased antibacterial activity particularly against Streptococcus pneumoniae strains. (C) 2009 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2009.03.024