1,1-dimethylethyl 3-(hydroxymethyl)-7α-methoxy-8-oxo-5-thia-1-azabicyclo<4.2.0>oct-3-ene-2-carboxylate | 116536-03-9

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 1,1-dimethylethyl 3-(hydroxymethyl)-7α-methoxy-8-oxo-5-thia-1-azabicyclo<4.2.0>oct-3-ene-2-carboxylate
• CAS: 116536-03-9
• 化学式: C₁₃H₁₉NO₅S
• 分子量: 301.364
• InChiKey: HJZAIIIIPKUKSR-CAWIPBJDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  20.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  76.07
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  1,1-dimethylethyl 3-(hydroxymethyl)-7α-methoxy-8-oxo-5-thia-1-azabicyclo<4.2.0>oct-3-ene-2-carboxylate 在 水 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 1.25h， 生成 1,1-dimethylethyl 3-<<(aminocarbonyl)oxy>methyl>-7α-methoxy-8-oxo-5-thia-1-azabicyclo<4.2.O>oct-3-ene-2-carboxylate
  参考文献：
  名称：

  Inhibition of human leukocyte elastase. 3. Synthesis and activity of 3'-substituted cephalosporins

  摘要：

  Several 3'-substituted cephalosporin sulfones were synthesized from 3-(hydroxymethyl)cephalosporin, which was prepared by Ti(OiPr)4 hydrolysis of the corresponding acetate. A method was also developed to prepare a 3-vinylcephalosporin. Some of these compound were found to be potent time-dependent inhibitors of human leukocyte elastase (HLE). The HLE inhibitory activity was correlated with sigma 1 and it was concluded that the potency was determined by the electron-withdrawing ability as well as the size of the substituent. A mechanism for inhibition of HLE by cephalosporin sulfones is proposed.

  DOI：

  10.1021/jm00171a030
• 作为产物：
  描述：

  1,1-dimethylethyl 3-<(acetyloxy)methyl>-7α-methoxy-8-oxo-5-thia-1-azabicyclo<4.2.0>oct-3-ene-2-carboxylate 在 titanium(IV) isopropylate 作用下， 以 异丙醇 为溶剂， 以61%的产率得到1,1-dimethylethyl 3-(hydroxymethyl)-7α-methoxy-8-oxo-5-thia-1-azabicyclo<4.2.0>oct-3-ene-2-carboxylate
  参考文献：
  名称：

  Inhibition of human leukocyte elastase. 3. Synthesis and activity of 3'-substituted cephalosporins

  摘要：

  Several 3'-substituted cephalosporin sulfones were synthesized from 3-(hydroxymethyl)cephalosporin, which was prepared by Ti(OiPr)4 hydrolysis of the corresponding acetate. A method was also developed to prepare a 3-vinylcephalosporin. Some of these compound were found to be potent time-dependent inhibitors of human leukocyte elastase (HLE). The HLE inhibitory activity was correlated with sigma 1 and it was concluded that the potency was determined by the electron-withdrawing ability as well as the size of the substituent. A mechanism for inhibition of HLE by cephalosporin sulfones is proposed.

  DOI：

  10.1021/jm00171a030