sodium;(2S)-2-[[2-acetyloxy-4-[(2-methylpropan-2-yl)oxycarbonylamino]benzoyl]amino]-3-(1H-indol-3-yl)propanoate | 1122102-44-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: sodium;(2S)-2-[[2-acetyloxy-4-[(2-methylpropan-2-yl)oxycarbonylamino]benzoyl]amino]-3-(1H-indol-3-yl)propanoate
• CAS: 1122102-44-6
• 化学式: C₂₅H₂₆N₃O₇*Na
• 分子量: 503.487
• InChiKey: LUNFLEWHOFCKBJ-BDQAORGHSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  -0.46
• 重原子数：
  36
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  150
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  sodium;(2S)-2-[[2-acetyloxy-4-[(2-methylpropan-2-yl)oxycarbonylamino]benzoyl]amino]-3-(1H-indol-3-yl)propanoate 在 盐酸 、 溶剂黄146 、 sodium hydroxide 作用下， 以 水 为溶剂， 反应 12.0h， 以73%的产率得到sodium;(2S)-2-[(4-amino-2-hydroxybenzoyl)amino]-3-(1H-indol-3-yl)propanoate
  参考文献：
  名称：

  Colon-specific mutual amide prodrugs of 4-aminosalicylic acid for their mitigating effect on experimental colitis in rats

  摘要：

  Mutual amide prodrugs of 4-aminosalicylic acid with D-phenylalanine and L-tryptophan were synthesized for targeted drug delivery to the inflamed gut tissue in inflammatory bowel disease. Stability studies in aqueous buffers (pH 1.2 and 7.4) showed that the synthesized prodrugs were stable in both the buffers over a period of 10 h. In rat fecal matter the release of 4-aminosalicylic acid from the prodrugs was in the range of 86-91% over a period of 20 h, with half-lives ranging between 343 and 412 min following first order kinetics. Targeting potential of the carrier system and the ameliorating effect of the amide conjugates were evaluated in trinitrobenzenesulfonic acid-induced experimental colitis model in rats. The prodrugs were assessed for their probable damaging effects on pancreas and liver with the help of histopathological analysis and for their ulcerogenic potential by Rainsford's cold stress method. They were found to have improved safety profile than sulfasalazine, oral 4- and 5-aminosalicylic acid with similar pharmacological spectrum and advantages of sulfasalazine. (C) 2008 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2008.03.035
• 作为产物：
  描述：

  [2-Carbonochloridoyl-5-[(2-methylpropan-2-yl)oxycarbonylamino]phenyl] acetate 、 L-色氨酸甲酯盐酸盐 在 sodium hydroxide 作用下， 以 水 为溶剂， 反应 38.0h， 以78%的产率得到sodium;(2S)-2-[[2-acetyloxy-4-[(2-methylpropan-2-yl)oxycarbonylamino]benzoyl]amino]-3-(1H-indol-3-yl)propanoate
  参考文献：
  名称：

  Colon-specific mutual amide prodrugs of 4-aminosalicylic acid for their mitigating effect on experimental colitis in rats

  摘要：

  Mutual amide prodrugs of 4-aminosalicylic acid with D-phenylalanine and L-tryptophan were synthesized for targeted drug delivery to the inflamed gut tissue in inflammatory bowel disease. Stability studies in aqueous buffers (pH 1.2 and 7.4) showed that the synthesized prodrugs were stable in both the buffers over a period of 10 h. In rat fecal matter the release of 4-aminosalicylic acid from the prodrugs was in the range of 86-91% over a period of 20 h, with half-lives ranging between 343 and 412 min following first order kinetics. Targeting potential of the carrier system and the ameliorating effect of the amide conjugates were evaluated in trinitrobenzenesulfonic acid-induced experimental colitis model in rats. The prodrugs were assessed for their probable damaging effects on pancreas and liver with the help of histopathological analysis and for their ulcerogenic potential by Rainsford's cold stress method. They were found to have improved safety profile than sulfasalazine, oral 4- and 5-aminosalicylic acid with similar pharmacological spectrum and advantages of sulfasalazine. (C) 2008 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2008.03.035