1,1-dimethylethyl 7α-methoxy-3-methyl-8-oxo-5-thia-1-azabicyclo<4.2.0>oct-2-ene-2-carboxylate | 95570-84-6

• 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 7α-methoxy-3-methyl-8-oxo-5-thia-1-azabicyclo<4.2.0>oct-2-ene-2-carboxylate
• 英文别名: tert-butyl (6R,7S)-7-methoxy-3-methyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate
• CAS: 95570-84-6
• 化学式: C₁₃H₁₉NO₄S
• 分子量: 285.364
• InChiKey: AWCWEOHLPVSAAS-GXSJLCMTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.53
• 重原子数：
  19.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  55.84
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  1,1-dimethylethyl 7α-methoxy-3-methyl-8-oxo-5-thia-1-azabicyclo<4.2.0>oct-2-ene-2-carboxylate 在 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 以76%的产率得到t-butyl 7α-methoxy-3-methyl-3-cephem-4-carboxylate 1,1-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：

  t-butyl 3-acetoxymethyl-7α-methoxy-3-cephem-4-carboxylate 在 palladium on activated charcoal 氢气 作用下， 以 乙醇 为溶剂， 反应 3.0h， 以47%的产率得到1,1-dimethylethyl 7α-methoxy-3-methyl-8-oxo-5-thia-1-azabicyclo<4.2.0>oct-2-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

文献信息

• Stereoselective alkoxy-de-amination of 7β-Amino-3-Deacetoxy cephalosporanic acid
  作者：Marco Alpegiani、Pierluigl Bissolino、Matteo D'Anello、Giovanni Rivola、Daniela Borghi、Ettore Perrone

  DOI：10.1016/s0040-4039(00)79404-4

  日期：1991.7

  The direct conversion of 7-ADCA into the corresponding 7α-alkoxy derivatives is described. This reaction constitutes the most convenient access to a new class of potent inhibitors of human leukocyte elastase.

  描述了将7-ADCA直接转化为相应的7α-烷氧基衍生物。该反应构成了最便捷的途径来获得一类新型的人类白细胞弹性蛋白酶的有效抑制剂。