6β-(2-phenyl-acetylamino)-penicillanic acid (Ξ)-5-oxo-2,5-dihydro-furan-2-yl ester | 39878-73-4

• 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: 6β-(2-phenyl-acetylamino)-penicillanic acid (Ξ)-5-oxo-2,5-dihydro-furan-2-yl ester
• 英文别名: 4-Thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid, 3,3-dimethyl-7-oxo-6-[(phenylacetyl)amino]-(2S,5R,6R)-, 2,5-dihydro-5-oxo-2-furanyl ester；(5-oxo-2H-furan-2-yl) (2S,5R,6R)-3,3-dimethyl-7-oxo-6-[(2-phenylacetyl)amino]-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate
• CAS: 39878-73-4
• 化学式: C₂₀H₂₀N₂O₆S
• 分子量: 416.455
• InChiKey: LUWWJTQSCMQHPH-YCXXCVGLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.76
• 重原子数：
  29.0
• 可旋转键数：
  5.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  102.01
• 氢给体数：
  1.0
• 氢受体数：
  7.0

反应信息

• 作为产物：
  描述：

  5-溴呋喃-2(5H)-酮 、 Penicillin G potassium 生成 6β-(2-phenyl-acetylamino)-penicillanic acid (Ξ)-5-oxo-2,5-dihydro-furan-2-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