4-[[2-(2-Carboxyethyl)phenyl]diazenyl]benzoic acid | 1415405-05-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 偶氮苯
• 英文名称: 4-[[2-(2-Carboxyethyl)phenyl]diazenyl]benzoic acid
• CAS: 1415405-05-8
• 化学式: C₁₆H₁₄N₂O₄
• 分子量: 298.298
• InChiKey: KIPMSWHHCNILAT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  99.3
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  3-[2-[[4-[(2-Methylpropan-2-yl)oxycarbonyl]phenyl]diazenyl]phenyl]propanoic acid 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 生成 4-[[2-(2-Carboxyethyl)phenyl]diazenyl]benzoic acid
  参考文献：
  名称：

  Structure requirements for anaerobe processing of azo compounds: Implications for prodrug design

  摘要：

  This Letter generalizes the metabolism of the azo class of compounds by Clostridium perfringens, an anaerobe found in the human colon. A recently reported 5-aminosalicylic acid-based prednisolone prodrug was shown to release the drug when incubated with the bacteria, while the para-aminobenzoic acid (PABA) based analogue did not. Instead, it showed a new HPLC peak with a relatively close retention time to the parent which was identified by LCMS as the partially reduced hydrazine product. This Letter investigates azoreduction across a panel of substrates with varying degrees of electronic and steric similarity to the PABA-based compound. Azo compounds with an electron donating group on the azo-containing aromatic ring showed immediate disproportionation to their parent amines without any detection of hydrazine intermediates by HPLC. Compounds containing only electron withdrawing groups are partially and reversibly reduced to produce a stable detectable hydrazine. They do not disproportionate to their parent amines, but regenerate the parent azo compound. This incomplete reduction is relevant to the design of azo-based prodrugs and the toxicology of azo-based dyes. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.10.014

文献信息

• Structure requirements for anaerobe processing of azo compounds: Implications for prodrug design
  作者：Jason Gavin、Juan F. Marquez Ruiz、Kinga Kedziora、Henry Windle、Dermot P. Kelleher、John F. Gilmer

  DOI：10.1016/j.bmcl.2012.10.014

  日期：2012.12

  This Letter generalizes the metabolism of the azo class of compounds by Clostridium perfringens, an anaerobe found in the human colon. A recently reported 5-aminosalicylic acid-based prednisolone prodrug was shown to release the drug when incubated with the bacteria, while the para-aminobenzoic acid (PABA) based analogue did not. Instead, it showed a new HPLC peak with a relatively close retention time to the parent which was identified by LCMS as the partially reduced hydrazine product. This Letter investigates azoreduction across a panel of substrates with varying degrees of electronic and steric similarity to the PABA-based compound. Azo compounds with an electron donating group on the azo-containing aromatic ring showed immediate disproportionation to their parent amines without any detection of hydrazine intermediates by HPLC. Compounds containing only electron withdrawing groups are partially and reversibly reduced to produce a stable detectable hydrazine. They do not disproportionate to their parent amines, but regenerate the parent azo compound. This incomplete reduction is relevant to the design of azo-based prodrugs and the toxicology of azo-based dyes. (C) 2012 Elsevier Ltd. All rights reserved.