(4R,5S,6S)-6-((R)-1-Hydroxy-ethyl)-3-[(2-hydroxy-ethyl)-methyl-thiocarbamoylsulfanyl]-4-methyl-7-oxo-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid 4-nitro-benzyl ester | 192883-71-9

• 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-[(2-hydroxy-ethyl)-methyl-thiocarbamoylsulfanyl]-4-methyl-7-oxo-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid 4-nitro-benzyl ester
• 英文别名: (4-nitrophenyl)methyl (4R,5S,6S)-6-[(1R)-1-hydroxyethyl]-3-[2-hydroxyethyl(methyl)carbamothioyl]sulfanyl-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate
• CAS: 192883-71-9
• 化学式: C₂₁H₂₅N₃O₇S₂
• 分子量: 495.577
• InChiKey: HTOFRFLDLOYVEL-CZPYZCIJSA-N

物化性质

• 沸点：
  700.4±70.0 °C(Predicted)
• 密度：
  1.49±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  33
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  194
• 氢给体数：
  2
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  (4R,5S,6S)-6-((R)-1-Hydroxy-ethyl)-3-[(2-hydroxy-ethyl)-methyl-thiocarbamoylsulfanyl]-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 氢气 、 碳酸氢钠 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， 生成 Sodium; (4R,5S,6S)-6-((R)-1-hydroxy-ethyl)-3-[(2-hydroxy-ethyl)-methyl-thiocarbamoylsulfanyl]-4-methyl-7-oxo-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylate
  参考文献：
  名称：

  Novel dithiocarbamate carbapenems with anti-MRSA activity

  摘要：

  A new series of 1 beta-methyl carbapenems, in which a disubstituted-aminothiocarbonylthio moiety was attached to the C-2 position of the carbapenem nucleus, were prepared and evaluated for anti-MRSA activity. These derivatives showed good in vitro antibacterial activity against high-level MRSA, and the finding of good affinity for PBP-2' supported these results. Some of the compounds having favorable protein-binding affinity showed excellent in vivo anti-MRSA activity. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(98)00069-8
• 作为产物：
  描述：

  杂氮双环磷酸酯 、 在 lithium chloride 作用下， 以 四氢呋喃 为溶剂， 生成 (4R,5S,6S)-6-((R)-1-Hydroxy-ethyl)-3-[(2-hydroxy-ethyl)-methyl-thiocarbamoylsulfanyl]-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：

  Novel dithiocarbamate carbapenems1 with anti-MRSA activity

  摘要：

  A new series of carbapenems, in which disubstituted-aminothiocarbonylthio moiety, directly attached to the C-2 position, were prepared and evaluated for their antibacterial potency. These analogs showed potent activity against high-level MRSA, Among them, 9e and 9i were found to exhibit good in vivo efficacy comparable to that of vancomycin, for mouse septicemia model with high-level MRSA. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0960-894x(97)00272-2