diphenylmethyl N-tosyl-S-aminosulfeniminocephalosporanate | 227009-40-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: diphenylmethyl N-tosyl-S-aminosulfeniminocephalosporanate
• 英文别名: benzhydryl (6R)-3-(acetyloxymethyl)-7-[(4-methylphenyl)sulfonylamino]sulfanylimino-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate
• CAS: 227009-40-7
• 化学式: C₃₀H₂₇N₃O₇S₃
• 分子量: 637.758
• InChiKey: SKQKWCNSTMIMMG-GDLZYMKVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  43
• 可旋转键数：
  12
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  190
• 氢给体数：
  1
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  重氮甲烷 、 diphenylmethyl N-tosyl-S-aminosulfeniminocephalosporanate 以 二氯甲烷 为溶剂， 反应 63.0h， 生成 diphenylmethyl N-methyl-N-tosyl-S-aminosulfeniminocephalosporanate
  参考文献：
  名称：

  Extending the β-Lactamase-Dependent Prodrug Armory: S-Aminosulfeniminocephalosporins as Dual-Release Prodrugs

  摘要：

  Cephalosporins bearing an S-aminosulfenimine (R'(R")NSN=) side chain at the 7-position are prototypic examples of a novel class of beta-lactamase-dependent prodrug. Enzyme-catalyzed hydrolysis of the p-lactam ring in these structures triggers release of both the 3'-acetoxy group and the side chain sulfur-attached S-amino moiety as R'(R")NH. This reactivity pattern should allow site-specific corelease of two distinct drug components from a cephalosporin, thereby providing a singular enhancement to the capacity of a cephalosporin as a prodrug nucleus; a key advantage of a dual-release prodrug is the potential to establish synergy between the coreleased structures. Areas for exploitation of this new structure type are antibody-directed enzyme prodrug therapy (ADEPT), which is a key emerging anticancer therapy, and the further development of site-specific-release prodrugs to combat the problem of beta-lactamase-based resistance to antibiotics.

  DOI：

  10.1021/jo981993a
• 作为产物：
  描述：

  二苯基重氮甲烷 以 甲醇 、 二氯甲烷 为溶剂， 反应 2.25h， 生成 diphenylmethyl N-tosyl-S-aminosulfeniminocephalosporanate
  参考文献：
  名称：

  Extending the β-Lactamase-Dependent Prodrug Armory: S-Aminosulfeniminocephalosporins as Dual-Release Prodrugs

  摘要：

  Cephalosporins bearing an S-aminosulfenimine (R'(R")NSN=) side chain at the 7-position are prototypic examples of a novel class of beta-lactamase-dependent prodrug. Enzyme-catalyzed hydrolysis of the p-lactam ring in these structures triggers release of both the 3'-acetoxy group and the side chain sulfur-attached S-amino moiety as R'(R")NH. This reactivity pattern should allow site-specific corelease of two distinct drug components from a cephalosporin, thereby providing a singular enhancement to the capacity of a cephalosporin as a prodrug nucleus; a key advantage of a dual-release prodrug is the potential to establish synergy between the coreleased structures. Areas for exploitation of this new structure type are antibody-directed enzyme prodrug therapy (ADEPT), which is a key emerging anticancer therapy, and the further development of site-specific-release prodrugs to combat the problem of beta-lactamase-based resistance to antibiotics.

  DOI：

  10.1021/jo981993a