4-[(4-Hydroxyphenyl)diazenyl]phthalic acid | 1417825-89-8

• 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-[(4-Hydroxyphenyl)diazenyl]phthalic acid
• CAS: 1417825-89-8
• 化学式: C₁₄H₁₀N₂O₅
• 分子量: 286.244
• InChiKey: PYCXKZLQEWOAEQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  120
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  4-氨基邻苯二甲酸 、 苯酚 在 盐酸 、 sodium nitrite 作用下， 以 水 为溶剂， 生成 4-[(4-Hydroxyphenyl)diazenyl]phthalic acid
  参考文献：
  名称：

  Design, synthesis and ex vivo evaluation of colon-specific azo based prodrugs of anticancer agents

  摘要：

  Colon-specific azo based prodrugs of anticancer agents like methotrexate (6), gemcitabine (7) and analogue of oxaliplatin (RTB-4) (8) were synthesized and characterized by modern analytical techniques. The prepared prodrugs were stable in acidic (pH 1.2) and basic (pH 7.4) buffers which showed their stability in upper GIT environment. Further, an assay was performed which demonstrated the presence of azoreductase enzyme in the rat fecal material, rat cecum content and other parts of intestinal content which reduce specifically the azo bond and release the drug. The in vitro cytotoxicity assay was also performed which clearly indicated that these azo based prodrugs are active against human colorectal cancer cell lines (COLO 205, COLO 320 DM and HT-29). The release behavior of prodrugs (10, 11 and 15) was 60-70% after 24 h incubation at 37 degrees C. Therefore, the synthesized azo linked prodrugs of methotrexate, gemcitabine and RTB-4 are the potential candidates for colon targeted drug delivery system with minimal undesirable side effects. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.07.059