3-[2-(N-Boc-L-alanyl-L-valyloxy)-4,6-dimethylphenyl]-3,3-dimethylpropionic acid | 380306-42-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 3-[2-(N-Boc-L-alanyl-L-valyloxy)-4,6-dimethylphenyl]-3,3-dimethylpropionic acid
• CAS: 380306-42-3
• 化学式: C₂₆H₄₀N₂O₇
• 分子量: 492.613
• InChiKey: AGHXXPLZJRXMFH-UWJYYQICSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.02
• 重原子数：
  35.0
• 可旋转键数：
  9.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  131.03
• 氢给体数：
  3.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  甲氧苯胺 、 3-[2-(N-Boc-L-alanyl-L-valyloxy)-4,6-dimethylphenyl]-3,3-dimethylpropionic acid 在 N,N'-二环己基碳二亚胺 、 1-羟基苯并三唑一水物 、 4-二甲氨基吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 0.34h， 以25%的产率得到N-(4-methoxyphenyl)-3-[2-(N-Boc-L-alanyl-L-valyloxy)-4,6-dimethylphenyl]-3,3-dimethylpropionamide
  参考文献：
  名称：

  Coumarin Derivatives as Protease-Sensitive Prodrugs

  摘要：

  To overcome the lack of selectivity of anticancer drugs toward malignant cells, the development of prodrugs, which could be activated selectively by tumour-specific proteases is the goal of these studies. In this work tripartate prodrugs have been evaluated consisting of a carrier unit and a spacer group, which allows for intramolecular cyclisation while releasing the third component, the compound attached to the carboxylic acid moiety of the spacer group. As carrier units amino acids or peptides have been used, which are required for recognition by the protease. As the spacer unit the "trimethyl-lock"-spacer has been applied; as a model leaving group p-anisidine was attached to the carboxylic acid moiety. It was intended to test the compounds for their releasing rate of p-anisidine. Two of the evaluated compounds, 9b and 9h, were degraded with half-lives of 46 min at room temperature. However, the poor solubility in aqueous solutions proved the major disadvantage of the TML-based prodrugs.

  DOI：

  10.1002/1521-4184(200106)334:6<209::aid-ardp209>3.0.co;2-y
• 作为产物：
  描述：

  1-O-(tert-butyldimethylsilyl)-3-[2-(N-Boc-L-alanyl-L-valyloxy)-4,6-dimethylphenyl]-3,3-dimethylpropan-1-ol 在 sodium chlorite 、 sodium dihydrogenphosphate 、 溶剂黄146 、 pyridinium chlorochromate 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 、 乙腈 为溶剂， 反应 1.0h， 生成 3-[2-(N-Boc-L-alanyl-L-valyloxy)-4,6-dimethylphenyl]-3,3-dimethylpropionic acid
  参考文献：
  名称：

  Coumarin Derivatives as Protease-Sensitive Prodrugs

  摘要：

  To overcome the lack of selectivity of anticancer drugs toward malignant cells, the development of prodrugs, which could be activated selectively by tumour-specific proteases is the goal of these studies. In this work tripartate prodrugs have been evaluated consisting of a carrier unit and a spacer group, which allows for intramolecular cyclisation while releasing the third component, the compound attached to the carboxylic acid moiety of the spacer group. As carrier units amino acids or peptides have been used, which are required for recognition by the protease. As the spacer unit the "trimethyl-lock"-spacer has been applied; as a model leaving group p-anisidine was attached to the carboxylic acid moiety. It was intended to test the compounds for their releasing rate of p-anisidine. Two of the evaluated compounds, 9b and 9h, were degraded with half-lives of 46 min at room temperature. However, the poor solubility in aqueous solutions proved the major disadvantage of the TML-based prodrugs.

  DOI：

  10.1002/1521-4184(200106)334:6<209::aid-ardp209>3.0.co;2-y