(4R,5S,6S)-6-((R)-1-Hydroxy-ethyl)-4-methyl-7-oxo-3-(4-pyridin-3-yl-thiazol-2-ylsulfanyl)-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid 4-nitro-benzyl ester | 161681-52-3

• 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: (4R,5S,6S)-6-((R)-1-Hydroxy-ethyl)-4-methyl-7-oxo-3-(4-pyridin-3-yl-thiazol-2-ylsulfanyl)-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid 4-nitro-benzyl ester
• CAS: 161681-52-3
• 化学式: C₂₅H₂₂N₄O₆S₂
• 分子量: 538.605
• InChiKey: PEUQTIWTOCDTBQ-UYVJDWJCSA-N

物化性质

• 沸点：
  784.7±70.0 °C(predicted)
• 密度：
  1.53±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.02
• 重原子数：
  37.0
• 可旋转键数：
  8.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  135.76
• 氢给体数：
  1.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  (4R,5S,6S)-6-((R)-1-Hydroxy-ethyl)-4-methyl-7-oxo-3-(4-pyridin-3-yl-thiazol-2-ylsulfanyl)-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid 4-nitro-benzyl ester 在 palladium on activated charcoal MOPS buffer 、 氢气 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 生成 (4R,5S,6S)-6-((R)-1-Hydroxy-ethyl)-4-methyl-7-oxo-3-(4-pyridin-3-yl-thiazol-2-ylsulfanyl)-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid
  参考文献：
  名称：

  Synthesis and biological properties of a new series of anti-MRSA β-lactams; 2-(thiazol-2-ylthio)carbapenems

  摘要：

  A series of 1 beta-methylcarbapenems containing variously C-2 substituted thiazol-2-ylthio groups were synthesized, and their in vitro anti-MRSA activity was examined. Among them, 1 beta-methyl-2-(4-arylthiazol-2-ylthio) carbapenems exhibited superior anti-MRSA activity. Introduction of a cationic moiety in the C-2 side chain not only reduced the binding to HSA but also increased the stability against DHP-I, without affecting the anti-MRSA, activity. It was also found that the distance between the cationic moiety and the carbapenem skeleton was related to the strength of HSA binding and the stability against DHP-I. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0968-0896(96)00273-8
• 作为产物：
  描述：

  2-mercapto-4-(3-pyridyl)thiazole 、 (4R,5R,6S,8R)-p-nitrobenzyl-3-(diphenylphosphoryloxy)-4-methyl-6-(1-(trimethylsilyloxy)ethyl)-7-oxo-1-azabicyclo<3.2.0>hept-2-ene-2-carboxylate 在 sodium hydride 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 18.0h， 生成 (4R,5S,6S)-6-((R)-1-Hydroxy-ethyl)-4-methyl-7-oxo-3-(4-pyridin-3-yl-thiazol-2-ylsulfanyl)-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid 4-nitro-benzyl ester
  参考文献：
  名称：

  Synthesis and biological properties of a new series of anti-MRSA β-lactams; 2-(thiazol-2-ylthio)carbapenems

  摘要：

  A series of 1 beta-methylcarbapenems containing variously C-2 substituted thiazol-2-ylthio groups were synthesized, and their in vitro anti-MRSA activity was examined. Among them, 1 beta-methyl-2-(4-arylthiazol-2-ylthio) carbapenems exhibited superior anti-MRSA activity. Introduction of a cationic moiety in the C-2 side chain not only reduced the binding to HSA but also increased the stability against DHP-I, without affecting the anti-MRSA, activity. It was also found that the distance between the cationic moiety and the carbapenem skeleton was related to the strength of HSA binding and the stability against DHP-I. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0968-0896(96)00273-8