1,1-dimethylethyl 3-(1-carboxy-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 | 127792-55-6

• 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 3-(1-carboxy-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
• 英文别名: (2S)-2-[[(6R,7S)-7-methoxy-2-[(2-methylpropan-2-yl)oxycarbonyl]-5,5,8-trioxo-5lambda6-thia-1-azabicyclo[4.2.0]oct-2-en-3-yl]methoxycarbonylamino]-3-phenylpropanoic acid；(2S)-2-[[(6R,7S)-7-methoxy-2-[(2-methylpropan-2-yl)oxycarbonyl]-5,5,8-trioxo-5λ6-thia-1-azabicyclo[4.2.0]oct-2-en-3-yl]methoxycarbonylamino]-3-phenylpropanoic acid
• CAS: 127792-55-6
• 化学式: C₂₃H₂₈N₂O₁₀S
• 分子量: 524.549
• InChiKey: VWDIAQLSGGZXOF-VDZJLULYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  36
• 可旋转键数：
  11
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  174
• 氢给体数：
  2
• 氢受体数：
  10

反应信息

• 作为产物：
  描述：

  1,1-dimethylethyl 3-(hydroxymethyl)-7α-methoxy-8-oxo-5-thia-1-azabicyclo<4.2.0>oct-3-ene-2-carboxylate 在 4-二甲氨基吡啶 、 苯甲醚 、 间氯过氧苯甲酸 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 0.53h， 生成 1,1-dimethylethyl 3-(1-carboxy-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

文献信息

• Inhibition of human leukocyte elastase. 3. Synthesis and activity of 3'-substituted cephalosporins
  作者：Shrenik K. Shah、Karen A. Brause、Gilbert O. Chandler、Paul E. Finke、Bonnie M. Ashe、Hazel Weston、Wilson B. Knight、Alan L. Maycock、James B. Doherty

  DOI：10.1021/jm00171a030

  日期：1990.9

  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.