N-<2-(tert-butoxycarbonyl)ethyl>-3-(acetoxymethyl)-7α-methoxy-8-oxo-5-thia-1-azabicyclo<4.2.0>oct-2-ene-2-carboxamide | 128495-28-3

• 分子结构分类: 有机化合物 - 有机杂环化合物
• 英文名称: N-<2-(tert-butoxycarbonyl)ethyl>-3-(acetoxymethyl)-7α-methoxy-8-oxo-5-thia-1-azabicyclo<4.2.0>oct-2-ene-2-carboxamide
• 英文别名: tert-butyl 3-[[(6R,7S)-3-(acetyloxymethyl)-7-methoxy-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carbonyl]amino]propanoate
• CAS: 128495-28-3
• 化学式: C₁₈H₂₆N₂O₇S
• 分子量: 414.48
• InChiKey: DOUWTOVLPRTEEG-WMLDXEAASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.58
• 重原子数：
  28.0
• 可旋转键数：
  7.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  111.24
• 氢给体数：
  1.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  N-<2-(tert-butoxycarbonyl)ethyl>-3-(acetoxymethyl)-7α-methoxy-8-oxo-5-thia-1-azabicyclo<4.2.0>oct-2-ene-2-carboxamide 、 N-<2-(tert-butoxycarbonyl)ethyl>-3-(acetoxymethyl)-7α-methoxy-8-oxo-5-thia-1-azabicyclo<4.2.0>oct-3-ene-2-carboxamide 、 间氯过氧苯甲酸 生成 N-<2-(tert-butoxycarbonyl)ethyl>-3-(acetoxymethyl)-7α-methoxy-8-oxo-5-thia-1-azabicyclo<4.2.0>oct-2-ene-2-carboxamide 5,5-dioxide
  参考文献：
  名称：

  FINKE, PAUL E.;ASHE, BONNIE M.;KNIGHT, WILSON B.;MAYCOCK, ALAN L.;NAVIA, +, J. MED. CHEM., 33,(1990) N, C. 2522-2528

  摘要：

  DOI：
• 作为产物：
  描述：

  t-butyl 3-acetoxymethyl-7α-methoxy-3-cephem-4-carboxylate 在 苯甲醚 、 N,N'-二环己基碳二亚胺 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 4.5h， 生成 N-<2-(tert-butoxycarbonyl)ethyl>-3-(acetoxymethyl)-7α-methoxy-8-oxo-5-thia-1-azabicyclo<4.2.0>oct-2-ene-2-carboxamide
  参考文献：
  名称：

  Inhibition of human leukocyte elastase. 2. Inhibition by substituted cephalosporin esters and amides

  摘要：

  A variety of 7 alpha-methoxycephalosporin ester and amide sulfones were prepared and tested to determine the structure-activity relations for inhibition of human leukocyte elastase (HLE), a serine protease which has been implicated in several degenerative lung and tissue diseases. The most potent IC50 values were obtained with neutral, lipophilic derivatives, with the esters being more active than the amides. However, the best time-dependent inhibition in this series was observed with the p- and m-carboxybenzyl esters 7b and 7c. These results are discussed in terms of the proposed mechanism of inhibition as well as a molecular modeling study using the recently solved X-ray crystal structure of HLE.

  DOI：

  10.1021/jm00171a029