(4S,5R,6S)-6-[(1R)-1-hydroxyethyl]-4-methyl-3-[6-[[3-[(4-methyl-1,4-diazoniabicyclo[2.2.2]octan-1-yl)methyl]phenyl]methyl]-7-methylsulfanylimidazo[5,1-b][1,3]thiazol-6-ium-2-yl]-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate;bromide;iodide | 1121706-87-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酰胺类
• 英文名称: (4S,5R,6S)-6-[(1R)-1-hydroxyethyl]-4-methyl-3-[6-[[3-[(4-methyl-1,4-diazoniabicyclo[2.2.2]octan-1-yl)methyl]phenyl]methyl]-7-methylsulfanylimidazo[5,1-b][1,3]thiazol-6-ium-2-yl]-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate;bromide;iodide
• CAS: 1121706-87-3
• 化学式: Br*C₃₁H₃₉N₅O₄S₂*I
• 分子量: 816.622
• InChiKey: NFOCAZRRSSVDMB-WEUNIZDUSA-L

计算性质

• 辛醇/水分配系数(LogP)：
  -4.82
• 重原子数：
  44
• 可旋转键数：
  7
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  143
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  4-Nitrobenzyl (1S,5R,6S)-6-((1R)-1-hydroxy-ethyl)-1-methyl-2-[6-[3-(4-methyl-1,4-diazoniabicyclo-[2,2,2]oct-1-yl)methylbenzyl]-7-methylthioimidazo[5,1-b]thiazolium-2-yl]-1-carbapen-2-em-3-carboxylate iodide dibromide 在 palladium on carbon 、 氢气 作用下， 以 四氢呋喃 、 水 为溶剂， 生成 (4S,5R,6S)-6-[(1R)-1-hydroxyethyl]-4-methyl-3-[6-[[3-[(4-methyl-1,4-diazoniabicyclo[2.2.2]octan-1-yl)methyl]phenyl]methyl]-7-methylsulfanylimidazo[5,1-b][1,3]thiazol-6-ium-2-yl]-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate;bromide;iodide
  参考文献：
  名称：

  Synthesis of novel di- and tricationic carbapenems with potent anti-MRSA activity

  摘要：

  A new series of 1 beta-methyl carbapenems possessing a 6,7-disubstituted imidazo[5,1-b]thiazol-2-yl group directly attached to the C-2 position of the carbapenem nucleus was prepared, and their activities against methicillin-resistant Staphylococcus aureus (MRSA) were evaluated. First, a benzyl moiety was introduced at the C-6 position of imidazo[5,1-b]thiazole attached to the carbapenem. These benzylated molecules showed potent anti-MRSA activity, but poor water solubility. In order to overcome this drawback, we designed and synthesized di- and tricationic carbapenems and finally discovered a novel carbapenem (15i), which exhibited excellent anti-MRSA activity and good water solubility. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2008.11.039