1,1-dimethylethyl 3-<1-<<<(4-methoxyphenyl)methyl>oxy>carbonyl>-2-phenylethyl>-1-L-<<(aminocarbonyl)oxy>methyl>-7α-methoxy-8-oxo-5-thia-1-azabicyclo<4.2.O>oct-3-ene-2-carboxylate | 127792-56-7

• 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-<1-<<<(4-methoxyphenyl)methyl>oxy>carbonyl>-2-phenylethyl>-1-L-<<(aminocarbonyl)oxy>methyl>-7α-methoxy-8-oxo-5-thia-1-azabicyclo<4.2.O>oct-3-ene-2-carboxylate
• CAS: 127792-56-7
• 化学式: C₃₀H₃₄N₂O₉S
• 分子量: 598.674
• InChiKey: AGSQCMBRPTVSCY-ZUZZFMILSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.46
• 重原子数：
  42.0
• 可旋转键数：
  10.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  129.7
• 氢给体数：
  1.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  1,1-dimethylethyl 3-<1-<<<(4-methoxyphenyl)methyl>oxy>carbonyl>-2-phenylethyl>-1-L-<<(aminocarbonyl)oxy>methyl>-7α-methoxy-8-oxo-5-thia-1-azabicyclo<4.2.O>oct-3-ene-2-carboxylate 在 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 以93%的产率得到1,1-dimethylethyl 3-<1-<<<(4-methoxyphenyl)methyl>oxy>carbonyl>-2-phenylethyl>-1-L-<<(aminocarbonyl)oxy>methyl>-7α-methoxy-8-oxo-5-thia-1-azabicyclo<4.2.O>oct-2-ene-2-carboxylate 5,5-dioxide
  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 、 4-二甲氨基吡啶 作用下， 以 异丙醇 为溶剂， 反应 0.5h， 生成 1,1-dimethylethyl 3-<1-<<<(4-methoxyphenyl)methyl>oxy>carbonyl>-2-phenylethyl>-1-L-<<(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