4-(3-(2-hydroxyethoxy-4-amino)phenylazo)-N,N-bis(2-hydroxyethyl)aniline | 126335-40-8

• 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-(3-(2-hydroxyethoxy-4-amino)phenylazo)-N,N-bis(2-hydroxyethyl)aniline
• 英文别名: 4-((3-(2-Hydroxyethoxy)-4-aminophenyl)azo)-N,N-bis(2-hydroxyethyl)aniline；2-[4-[[4-amino-3-(2-hydroxyethoxy)phenyl]diazenyl]-N-(2-hydroxyethyl)anilino]ethanol
• CAS: 126335-40-8
• 化学式: C₁₈H₂₄N₄O₄
• 分子量: 360.413
• InChiKey: NYRMBOQKELPCIA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  26
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  124
• 氢给体数：
  4
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  在 水 、 sodium hydroxide 作用下， 以 乙醇 为溶剂， 反应 2.0h， 以1 g的产率得到4-(3-(2-hydroxyethoxy-4-amino)phenylazo)-N,N-bis(2-hydroxyethyl)aniline
  参考文献：
  名称：

  Synthesis and characterization of selected 4,4′-diaminoalkoxyazobenzenes

  摘要：

  The role of the -N(CH2CH2OH)(2) group in producing a mutagenic response from 4-((3-(2-hydroxyethoxy) 4-amino)phenylazo)-N,N-bis(2-hydroxyethyl)aniline has been investigated. To accomplish this goal, a group of substituted 4,4'-diaminoazobenzene dyes was synthesized, and their structures were confirmed using 1H NMR, TOF-LC-ESI mass spectrometry, and combustion analysis. Mutagenicity was determined using the standard Ames test in Salmonella strains TA98, TA100, and TA1538 with and without S9 enzyme activation. The results of this study provide evidence that the mutagenicity of the parent dye arises from the metabolic cleavage of N-hydroxyethyl groups to give the corresponding -NHCH2CH2OH and -NH2 substituted monoazo dyes as direct-acting mutagens. All 5 of the dyes studied were mutagenic at various levels with and without S9 enzyme activation in TA1538. In addition, the results show that removing one N-hydroxyethyl group and capping both -OH groups in the parent dye did not affect mutagenicity, whereas removing both N-hydroxyethyl groups produced a strong direct-acting mutagen in all three bacterial strains. Increasing the length of the N-alkyl chain from two to three carbon atoms eliminated mutagenicity in TA98 without S9 activation. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.dyepig.2010.03.002

文献信息

• Synthesis and characterization of selected 4,4′-diaminoalkoxyazobenzenes
  作者：Euigyung Jeong、Harold S. Freeman、Larry D. Claxton

  DOI：10.1016/j.dyepig.2010.03.002

  日期：2010.10

  The role of the -N(CH2CH2OH)(2) group in producing a mutagenic response from 4-((3-(2-hydroxyethoxy) 4-amino)phenylazo)-N,N-bis(2-hydroxyethyl)aniline has been investigated. To accomplish this goal, a group of substituted 4,4'-diaminoazobenzene dyes was synthesized, and their structures were confirmed using 1H NMR, TOF-LC-ESI mass spectrometry, and combustion analysis. Mutagenicity was determined using the standard Ames test in Salmonella strains TA98, TA100, and TA1538 with and without S9 enzyme activation. The results of this study provide evidence that the mutagenicity of the parent dye arises from the metabolic cleavage of N-hydroxyethyl groups to give the corresponding -NHCH2CH2OH and -NH2 substituted monoazo dyes as direct-acting mutagens. All 5 of the dyes studied were mutagenic at various levels with and without S9 enzyme activation in TA1538. In addition, the results show that removing one N-hydroxyethyl group and capping both -OH groups in the parent dye did not affect mutagenicity, whereas removing both N-hydroxyethyl groups produced a strong direct-acting mutagen in all three bacterial strains. Increasing the length of the N-alkyl chain from two to three carbon atoms eliminated mutagenicity in TA98 without S9 activation. (C) 2010 Elsevier Ltd. All rights reserved.