(4R,5S,6S)-6-((R)-1-Hydroxy-ethyl)-3-(4-isoquinolin-7-yl-thiazol-2-ylsulfanyl)-4-methyl-7-oxo-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid 4-nitro-benzyl ester | 161681-66-9

• 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)-3-(4-isoquinolin-7-yl-thiazol-2-ylsulfanyl)-4-methyl-7-oxo-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid 4-nitro-benzyl ester
• CAS: 161681-66-9
• 化学式: C₂₉H₂₄N₄O₆S₂
• 分子量: 588.665
• InChiKey: QMLLRUFOZJNRBY-KQACMCHDSA-N

物化性质

• 沸点：
  835.0±75.0 °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)：
  5.17
• 重原子数：
  41.0
• 可旋转键数：
  8.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.24
• 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)-3-(4-isoquinolin-7-yl-thiazol-2-ylsulfanyl)-4-methyl-7-oxo-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-[(1R)-1-hydroxyethyl]-3-[(4-isoquinolin-7-yl-1,3-thiazol-2-yl)sulfanyl]-4-methyl-7-oxo-1-azabicyclo[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：

  2,2,2-Trifluoro-1-[7-(2-tritylsulfanyl-thiazol-4-yl)-3,4-dihydro-1H-isoquinolin-2-yl]-ethanone 在 palladium on activated charcoal sodium hydroxide 、 sodium hydride 作用下， 以 四氢呋喃 、 甲醇 、 甲苯 为溶剂， 反应 25.5h， 生成 (4R,5S,6S)-6-((R)-1-Hydroxy-ethyl)-3-(4-isoquinolin-7-yl-thiazol-2-ylsulfanyl)-4-methyl-7-oxo-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