L-phenylalanine 4-methoxybenzyl ester | 47171-46-0

• 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: L-phenylalanine 4-methoxybenzyl ester
• 英文别名: (4-methoxyphenyl) (2S)-2-amino-3-phenylpropanoate
• CAS: 47171-46-0
• 化学式: C₁₆H₁₇NO₃
• 分子量: 271.316
• InChiKey: JFVZPQLSIFEGKK-HNNXBMFYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.17
• 重原子数：
  20.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  61.55
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  L-phenylalanine 4-methoxybenzyl ester 、 1,1-dimethylethyl 3-(hydroxymethyl)-7α-methoxy-8-oxo-5-thia-1-azabicyclo<4.2.0>oct-3-ene-2-carboxylate 、 N,N'-羰基二咪唑 在 4-二甲氨基吡啶 作用下， 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

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.