2-[2-[[4-Hydroxy-3-[(2-methylpropan-2-yl)oxycarbonyl]phenyl]diazenyl]phenyl]-2-methylpropanoic acid | 1422054-54-3

• 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: 2-[2-[[4-Hydroxy-3-[(2-methylpropan-2-yl)oxycarbonyl]phenyl]diazenyl]phenyl]-2-methylpropanoic acid
• CAS: 1422054-54-3
• 化学式: C₂₁H₂₄N₂O₅
• 分子量: 384.432
• InChiKey: KNBMAOGGKZMARZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  28
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  109
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  2-[2-[[4-Hydroxy-3-[(2-methylpropan-2-yl)oxycarbonyl]phenyl]diazenyl]phenyl]-2-methylpropanoic acid 、 (S)-16alpha,17-(丁亚基二氧基)-11beta,21-二羟基孕甾-1,4-二烯-3,20-二酮 在 偶氮二甲酸二异丙酯 、 三苯基膦 、 三氟乙酸 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成
  参考文献：
  名称：

  Azo-reductase activated budesodine prodrugs for colon targeting

  摘要：

  Budesodine is a synthetic glurocorticoid that undergoes substantial first pass metabolism, limiting systemic exposure. Its use in treatment of inflammatory bowel disease would benefit from a targeting strategy that could lead to a local topical effect, improving safety and increasing anti-inflammatory efficacy. A two-step prodrug strategy involving azoreduction/cyclization that we developed previously for prednisolone is here applied with some variations to budesonide. The budesodine prodrugs were tested using an in vitro azoreductase assay simulating human colonic microflora. The kinetics of amino steroid ester cyclization and its pH dependence was also evaluated. The stability of the prodrugs systems in simulated human duodenal and gastric fluid was evaluated to determine the likelihood of intact intestinal transit. The propionic acid derived prodrug 3 undergoes rapid activation by Clostridium perfingens and its putative reduction product cyclizes with acceptable rapidity when synthesized independently. These properties of 3 suggest that it has potential in management of ulcerative colitis. (c) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.10.006
• 作为产物：
  描述：

  2-甲基-2-(2-硝基苯基)丙酸甲酯 在 potassium peroxymonosulfate 、 palladium on activated charcoal 、 水 、 氢气 、 溶剂黄146 、 sodium hydroxide 作用下， 以 水 为溶剂， 生成 2-[2-[[4-Hydroxy-3-[(2-methylpropan-2-yl)oxycarbonyl]phenyl]diazenyl]phenyl]-2-methylpropanoic acid
  参考文献：
  名称：

  Azo-reductase activated budesodine prodrugs for colon targeting

  摘要：

  Budesodine is a synthetic glurocorticoid that undergoes substantial first pass metabolism, limiting systemic exposure. Its use in treatment of inflammatory bowel disease would benefit from a targeting strategy that could lead to a local topical effect, improving safety and increasing anti-inflammatory efficacy. A two-step prodrug strategy involving azoreduction/cyclization that we developed previously for prednisolone is here applied with some variations to budesonide. The budesodine prodrugs were tested using an in vitro azoreductase assay simulating human colonic microflora. The kinetics of amino steroid ester cyclization and its pH dependence was also evaluated. The stability of the prodrugs systems in simulated human duodenal and gastric fluid was evaluated to determine the likelihood of intact intestinal transit. The propionic acid derived prodrug 3 undergoes rapid activation by Clostridium perfingens and its putative reduction product cyclizes with acceptable rapidity when synthesized independently. These properties of 3 suggest that it has potential in management of ulcerative colitis. (c) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.10.006