4-[(2,5-Dioxoimidazolidin-4-ylidene)methyl]benzoic acid | 431940-27-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑烷类
• 英文名称: 4-[(2,5-Dioxoimidazolidin-4-ylidene)methyl]benzoic acid
• CAS: 431940-27-1
• 化学式: C₁₁H₈N₂O₄
• 分子量: 232.196
• InChiKey: WUTHPFGNYBVSDZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  95.5
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-[(2,5-Dioxoimidazolidin-4-ylidene)methyl]benzoic acid 在 palladium on activated charcoal 、 氢气 作用下， 以 甲醇 为溶剂， 反应 8.0h， 生成 5-(4'-carboxybenzyl)hydantoin
  参考文献：
  名称：

  Biotransformation of new racemic (R,S)-5-benzylhydantoin derivatives by D-hydantoinases from adzuki bean

  摘要：

  In the present work the scope of D-hydantoinase enzyme application was increased towards new racemic (R, S) -5-benzylhydantoin derivatives. Five new substrates for the D-hydantoinase (R,S)-5-(3'-carboxybenzyl) hydantoin, (R, S)-5-(4'carboxybenzyl) hydantoin, (R,S)-5-(2'-carbomethoxybenzyl) hydantoin, (R,S)-5-(3'-carbomethoxybenzyl) hydantoin and (R,S)-5-(4'(4-ethoxycarboxy) propoxybenzyl) hydantoin were synthesised and converted using a two-step hydantoinase process into their corresponding D-phenylalanine derivatives. In this study two D-hydantoinases from Vigna angularis (adzuki bean) obtained from commercial sources were used: pure, isolated directly from Vigna angularis (V.a.D-HYD) 494 U/g and immobilised, recombinant, cloned and expressed in Escherichia coli (rD-HYD) 53.1 U/g. The results obtained showed that the examined enzymes catalysed hydrolysis of all new substrates into their corresponding N-carbamoyl-D-phenylalanine derivatives. High enantiomeric purities of the resulting D-phenylalanine derivatives were also determined. However, very low conversion yields of (R,S)-5-(3'-carboxybenzyl) hydantoin and (R, S)-5-(2'-carbomethoxybenzyl) hydantoin to corresponding N-carbamoyl-D amino acid were observed. Three D-phenylalanine derivatives: 4-carboxy-D-phenylalanine, 3-carbomethoxy-D-phenylalanine and 4-carbopropoxy-D-phenylalanine were obtained and isolated from the reaction mixtures using ion-exchange chromatography.

  DOI：

  10.3109/10242422.2014.893578
• 作为产物：
  描述：

  海因 、 对醛基苯甲酸 在 溶剂黄146 作用下， 生成 4-[(2,5-Dioxoimidazolidin-4-ylidene)methyl]benzoic acid
  参考文献：
  名称：

  Biotransformation of new racemic (R,S)-5-benzylhydantoin derivatives by D-hydantoinases from adzuki bean

  摘要：

  In the present work the scope of D-hydantoinase enzyme application was increased towards new racemic (R, S) -5-benzylhydantoin derivatives. Five new substrates for the D-hydantoinase (R,S)-5-(3'-carboxybenzyl) hydantoin, (R, S)-5-(4'carboxybenzyl) hydantoin, (R,S)-5-(2'-carbomethoxybenzyl) hydantoin, (R,S)-5-(3'-carbomethoxybenzyl) hydantoin and (R,S)-5-(4'(4-ethoxycarboxy) propoxybenzyl) hydantoin were synthesised and converted using a two-step hydantoinase process into their corresponding D-phenylalanine derivatives. In this study two D-hydantoinases from Vigna angularis (adzuki bean) obtained from commercial sources were used: pure, isolated directly from Vigna angularis (V.a.D-HYD) 494 U/g and immobilised, recombinant, cloned and expressed in Escherichia coli (rD-HYD) 53.1 U/g. The results obtained showed that the examined enzymes catalysed hydrolysis of all new substrates into their corresponding N-carbamoyl-D-phenylalanine derivatives. High enantiomeric purities of the resulting D-phenylalanine derivatives were also determined. However, very low conversion yields of (R,S)-5-(3'-carboxybenzyl) hydantoin and (R, S)-5-(2'-carbomethoxybenzyl) hydantoin to corresponding N-carbamoyl-D amino acid were observed. Three D-phenylalanine derivatives: 4-carboxy-D-phenylalanine, 3-carbomethoxy-D-phenylalanine and 4-carbopropoxy-D-phenylalanine were obtained and isolated from the reaction mixtures using ion-exchange chromatography.

  DOI：

  10.3109/10242422.2014.893578

文献信息

• Syntheses and studies of hydantoin derivatives as potential anti-tuberculosis inhibitors
  作者：Yan Liu、Wu Zhong、Song Li

  DOI：10.1016/j.cclet.2011.11.017

  日期：2012.2

  A short and efficient synthesis of (Z)-2-substituted-5-(4-((2-substitued-5-oxoimidazolidin-4-ylidene)methyl)benzamido)benzoic acid derivatives (8a-g) as potential type of FabH inhibitors is described. Their structures were confirmed by MS, NOE and H-1 NMR. (C) 2011 Wu Zhong. Published by Elsevier B.V. on behalf of Chinese Chemical Society. All rights reserved.