benzhydryl 7-(allyloxycarbonylamino)cephalosporinate | 805231-42-9

• 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: benzhydryl 7-(allyloxycarbonylamino)cephalosporinate
• 英文别名: benzhydryl (6R,7R)-3-(acetyloxymethyl)-8-oxo-7-(prop-2-enoxycarbonylamino)-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate
• CAS: 805231-42-9
• 化学式: C₂₇H₂₆N₂O₇S
• 分子量: 522.579
• InChiKey: SADYWEUQHAPPPG-PXDATVDWSA-N

物化性质

• 熔点：
  68-70 °C (decomp)
• 沸点：
  712.0±60.0 °C(Predicted)
• 密度：
  1.37±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  37
• 可旋转键数：
  12
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  137
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  benzhydryl 7-(allyloxycarbonylamino)cephalosporinate 在 三氟乙酸 、 三氟乙酸酐 作用下， 以 二氯甲烷 为溶剂， 反应 0.17h， 以74%的产率得到7-(allyloxycarbonylamino)cephalosporanic acid
  参考文献：
  名称：

  Toward the Development of a Cephalosporin-Based Dual-Release Prodrug for Use in ADEPT

  摘要：

  In previous work we have shown that a cephalosporin structure bearing an S-aminosulfenimine at the 7-position behaved as a beta-lactamase-dependent dual-release prodrug. Scission of the beta-lactam ring of such a structure led to the rapid loss of the sulfur-attached side chain moiety via an intramolecular displacement, while the T-group was lost via the well-established elimination process at that position. In the present work we report on an evaluation of the scope and limitations of exploiting the S-aminosulfenimine functionality to generate a cephalosporin-based prodrug incorporating two biologically active components. Starting from 7-ACA, a viable synthetic cycle was put in place that avoided formation of the Delta(2) isomer throughout and that allowed incorporation of aminoglutethimide at the 3'-position and of a tosyl S-aminosulfenimine at the 7-position. The direct incorporation of a biologically active sulfonamide (ethoxzolamide) or a sulfamate (coumate) at this latter position was not achieved as a result of the difficulty of generating the corresponding sulfur diimides. An indirect route for the formation of an S-aminosulfenimine was put in place, as was a general method of alkylation (Mitsunobu reaction) of the tosyl S-ammosulfenimine following its incorporation.

  DOI：

  10.1021/jo048970i
• 作为产物：
  描述：

  二苯基重氮甲烷 在 吡啶 、 4-二甲氨基吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 76.5h， 生成 benzhydryl 7-(allyloxycarbonylamino)cephalosporinate
  参考文献：
  名称：

  Toward the Development of a Cephalosporin-Based Dual-Release Prodrug for Use in ADEPT

  摘要：

  In previous work we have shown that a cephalosporin structure bearing an S-aminosulfenimine at the 7-position behaved as a beta-lactamase-dependent dual-release prodrug. Scission of the beta-lactam ring of such a structure led to the rapid loss of the sulfur-attached side chain moiety via an intramolecular displacement, while the T-group was lost via the well-established elimination process at that position. In the present work we report on an evaluation of the scope and limitations of exploiting the S-aminosulfenimine functionality to generate a cephalosporin-based prodrug incorporating two biologically active components. Starting from 7-ACA, a viable synthetic cycle was put in place that avoided formation of the Delta(2) isomer throughout and that allowed incorporation of aminoglutethimide at the 3'-position and of a tosyl S-aminosulfenimine at the 7-position. The direct incorporation of a biologically active sulfonamide (ethoxzolamide) or a sulfamate (coumate) at this latter position was not achieved as a result of the difficulty of generating the corresponding sulfur diimides. An indirect route for the formation of an S-aminosulfenimine was put in place, as was a general method of alkylation (Mitsunobu reaction) of the tosyl S-ammosulfenimine following its incorporation.

  DOI：

  10.1021/jo048970i