6β-(2-phenyl-acetylamino)-penicillanic acid (Ξ)-3-oxo-1,3-dihydro-benzo[c]thiophen-1-yl ester | 40125-38-0

• 英文名称: 6β-(2-phenyl-acetylamino)-penicillanic acid (Ξ)-3-oxo-1,3-dihydro-benzo[c]thiophen-1-yl ester
• 英文别名: 6β-(2-phenyl-acetylamino)-penicillanic acid (Ξ)-3-oxo-1,3-dihydro-benzo[c]thiophen-1-yl ester
• CAS: 40125-38-0
• 化学式: C₂₄H₂₂N₂O₅S₂
• 分子量: 482.581
• InChiKey: NAJKRLHCRWKWIW-MLYQTBBXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.91
• 重原子数：
  33.0
• 可旋转键数：
  5.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  92.78
• 氢给体数：
  1.0
• 氢受体数：
  7.0

反应信息

• 作为产物：
  描述：

  Penicillin G potassium 、 3-bromobenzothiophene-1(3H)-one 以 N,N-二甲基甲酰胺 为溶剂， 生成 6β-(2-phenyl-acetylamino)-penicillanic acid (Ξ)-3-oxo-1,3-dihydro-benzo[c]thiophen-1-yl ester
  参考文献：
  名称：

  Preparation, hydrolysis, and oral absorption of lactonyl esters of penicillins

  摘要：

  Lactonyl esters of ampicillin and other penicillins have been synthesized as prodrugs designed to improve the oral absorption of the parent penicillins. In general, the esters hydrolyzed rapidly in the presence of tissues including blood and certain of the esters were better absorbed than the parent penicillin. The phthalidyl ester of ampicillin [talampicillin (British Pharmacopoeia approved name), BRL 8988] was selected for extended studies. The compound was found to be well absorbed in various animal species and gave ampicillin serum concentrations in fasting human volunteers 2.5-3 times those obtained for ampicillin itself.

  DOI：

  10.1021/jm00234a007