phthalimidomethylampicillin

• 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: phthalimidomethylampicillin
• 英文别名: (1,3-dioxoisoindol-2-yl)methyl (2S,5R,6R)-6-[[(2R)-2-amino-2-phenylacetyl]amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate
• 化学式: C₂₅H₂₄N₄O₆S
• 分子量: 508.555
• InChiKey: QCIMRPCIJWIDMQ-PRHHBONVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  36
• 可旋转键数：
  7
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  164
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  phthalimidomethylampicillin 在 phosphate buffer 、 sodium chloride 作用下， 以 水 为溶剂， 生成 氨苄西林
  参考文献：
  名称：

  Ester prodrugs of ampicillin tailored for intracellular accumulation

  摘要：

  Seven new ester prodrugs of ampicillin with hydrolysis half-lives ranging from 65 to 308 min were synthesized. The cellular accumulation of two of them (in J774 mouse macrophages) and their activities against intracellular Staphylococcus aureus were determined in comparison with the pivaloyloxymethylester of ampicillin (pivampicillin) and ampicillin. The esters accumulated extensively and were more active than ampicillin in this in vitro system. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0960-894x(97)10146-9
• 作为产物：
  描述：

  氨苄西林 在 盐酸 、 potassium hydrogencarbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 36.33h， 生成 phthalimidomethylampicillin
  参考文献：
  名称：

  Ester prodrugs of ampicillin tailored for intracellular accumulation

  摘要：

  Seven new ester prodrugs of ampicillin with hydrolysis half-lives ranging from 65 to 308 min were synthesized. The cellular accumulation of two of them (in J774 mouse macrophages) and their activities against intracellular Staphylococcus aureus were determined in comparison with the pivaloyloxymethylester of ampicillin (pivampicillin) and ampicillin. The esters accumulated extensively and were more active than ampicillin in this in vitro system. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0960-894x(97)10146-9

文献信息

• Ester prodrugs of ampicillin tailored for intracellular accumulation
  作者：H.-J. Fan、I. Paternotte、M. Vermander、K. Li、M. Beaujean、B. Scorneaux、P. Dumont、P. Osinski、M. Claesen、P.M. Tulkens、E. Sonveaux

  DOI：10.1016/s0960-894x(97)10146-9

  日期：1997.12

  Seven new ester prodrugs of ampicillin with hydrolysis half-lives ranging from 65 to 308 min were synthesized. The cellular accumulation of two of them (in J774 mouse macrophages) and their activities against intracellular Staphylococcus aureus were determined in comparison with the pivaloyloxymethylester of ampicillin (pivampicillin) and ampicillin. The esters accumulated extensively and were more active than ampicillin in this in vitro system. (C) 1997 Elsevier Science Ltd.