(4R,5S,6S,8R)-3-[4-(1-aminocarbonylmethyl-pyridinio-4-yl)thiazol-2-ylthio]-4-methyl-6-(1-hydroxyethyl)-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate

• 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,8R)-3-[4-(1-aminocarbonylmethyl-pyridinio-4-yl)thiazol-2-ylthio]-4-methyl-6-(1-hydroxyethyl)-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate
• 英文别名: (4R,5S,6S)-3-[[4-[1-(2-amino-2-oxoethyl)pyridin-1-ium-4-yl]-1,3-thiazol-2-yl]sulfanyl]-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate
• 化学式: C₂₀H₂₀N₄O₅S₂
• 分子量: 460.535
• InChiKey: RRTBMNWYYYTAEH-XEQNPHJVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  31
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  194
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  2-巯基-4-(4-吡啶基)噻唑 在 palladium on activated charcoal potassium phosphate buffer 、 氢气 、 sodium hydride 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 28.0h， 生成 (4R,5S,6S,8R)-3-[4-(1-aminocarbonylmethyl-pyridinio-4-yl)thiazol-2-ylthio]-4-methyl-6-(1-hydroxyethyl)-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate
  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

文献信息

• Synthesis and biological properties of a new series of anti-MRSA β-lactams; 2-(thiazol-2-ylthio)carbapenems
  作者：Hisatoshi Shinagawa、Hiroshi Yamaga、Hitoshi Houchigai、Yoshihiro Sumita、Makoto Sunagawa

  DOI：10.1016/s0968-0896(96)00273-8

  日期：1997.3

  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.