p-nitrobenzyl (1R,5S,6S)-6-[(R)-1-hydroxyethyl]-2-[[N-(4-hydroxymethylbenzyl)-N-methyl]aminothiocarbonylthio]-1-methyl-1-carbapen-2-em-3-carboxylate | 268541-94-2

• 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: p-nitrobenzyl (1R,5S,6S)-6-[(R)-1-hydroxyethyl]-2-[[N-(4-hydroxymethylbenzyl)-N-methyl]aminothiocarbonylthio]-1-methyl-1-carbapen-2-em-3-carboxylate
• CAS: 268541-94-2
• 化学式: C₂₇H₂₉N₃O₇S₂
• 分子量: 571.675
• InChiKey: IFHMNMAPIBKGBY-AHWCRGGASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.35
• 重原子数：
  39.0
• 可旋转键数：
  9.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  133.45
• 氢给体数：
  2.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  p-nitrobenzyl (1R,5S,6S)-6-[(R)-1-hydroxyethyl]-2-[[N-(4-hydroxymethylbenzyl)-N-methyl]aminothiocarbonylthio]-1-methyl-1-carbapen-2-em-3-carboxylate 在 二异丙胺 、 sodium iodide 作用下， 以 四氢呋喃 、 丙酮 、 乙腈 为溶剂， 反应 4.0h， 生成
  参考文献：
  名称：

  Dicationic dithiocarbamate carbapenems with anti-MRSA activity

  摘要：

  A new class of 1 beta -methylcarbapenems bearing a doubly quaternarized 1,4-diazabicyclooctane (DABCO) substituted dithiocarbamate moiety at the C-2 side chain was prepared, and the biological profiles of the compounds, including in vitro and in vivo anti-MRSA activity and DHP-I susceptibility, were evaluated to identify a carbapenem derivative that was superior to BO-3482 (1). As a result, we discovered a 1 beta -methyl-2-[4-(4-carbamoylmethyl- 1,4-diazabicyclo[2,2,2]octanediium-1-yl)methyl-1,2,3,6-tetrahydropyridinylthiocarbonylthio] carbapenem, 14a showing greater than 2-fold better anti-MRSA activity in a mo use infection model and 3-fold better DHP-I susceptibility as compared with BO-3482 (1). (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(01)00044-x
• 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， 以42%的产率得到p-nitrobenzyl (1R,5S,6S)-6-[(R)-1-hydroxyethyl]-2-[[N-(4-hydroxymethylbenzyl)-N-methyl]aminothiocarbonylthio]-1-methyl-1-carbapen-2-em-3-carboxylate
  参考文献：
  名称：

  Dicationic dithiocarbamate carbapenems with anti-MRSA activity

  摘要：

  A new class of 1 beta -methylcarbapenems bearing a doubly quaternarized 1,4-diazabicyclooctane (DABCO) substituted dithiocarbamate moiety at the C-2 side chain was prepared, and the biological profiles of the compounds, including in vitro and in vivo anti-MRSA activity and DHP-I susceptibility, were evaluated to identify a carbapenem derivative that was superior to BO-3482 (1). As a result, we discovered a 1 beta -methyl-2-[4-(4-carbamoylmethyl- 1,4-diazabicyclo[2,2,2]octanediium-1-yl)methyl-1,2,3,6-tetrahydropyridinylthiocarbonylthio] carbapenem, 14a showing greater than 2-fold better anti-MRSA activity in a mo use infection model and 3-fold better DHP-I susceptibility as compared with BO-3482 (1). (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(01)00044-x