methyl (E)-6-(2-amino-3-cyano-6-methoxy-4,5-dimethylphenyl)-4-methylhex-4-enoate | 182011-48-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: methyl (E)-6-(2-amino-3-cyano-6-methoxy-4,5-dimethylphenyl)-4-methylhex-4-enoate
• CAS: 182011-48-9
• 化学式: C₁₈H₂₄N₂O₃
• 分子量: 316.4
• InChiKey: IUSHNXHKDWGBIV-IZZDOVSWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  23
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  85.3
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  methyl (E)-6-(2-amino-3-cyano-6-methoxy-4,5-dimethylphenyl)-4-methylhex-4-enoate 在 lithium hydroxide 作用下， 以 乙二醇二甲醚 为溶剂， 反应 2.0h， 生成 (E)-6-(2-amino-3-cyano-6-methoxy-4,5-dimethylphenyl)-4-methyl-4-hexenoic acid
  参考文献：
  名称：

  Structure−Activity Relationships for Inhibition of Inosine Monophosphate Dehydrogenase by Nuclear Variants of Mycophenolic Acid

  摘要：

  Structure-activity relationships in the region of the phthalide ring of the inosine monophosphate dehydrogenase inhibitor mycophenolic acid have been explored. Replacement of the lactone ring with other cyclic moieties resulted in loss of potency, especially for larger groups. Replacement of the ring by acyclic substituents also indicated a strong sensitivity to steric bulk. A phenolic hydroxyl group, with an adjacent hydrogen bond acceptor, was found to be essential for high potency. The aromatic methyl group was essential for activity; the methoxyl group could be replaced by ethyl to give a compound with 2-4 times the potency of mycophenolic acid in vitro and in vivo.

  DOI：

  10.1021/jm9603633
• 作为产物：
  描述：

  2,3,6-三甲基苯酚 在 palladium on activated charcoal 4-二甲氨基吡啶 、 ammonium hydroxide 、 N-溴代丁二酰亚胺(NBS) 、 四(三苯基膦)钯 、 氢气 、 叔丁基锂 、 硝酸 、 sodium acetate 、 tetra-N-butylammonium tribromide 、 potassium carbonate 、 对甲苯磺酸 、 三氟乙酸 、 三甲基乙酸 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 甲醇 、 乙醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 60.0h， 生成 methyl (E)-6-(2-amino-3-cyano-6-methoxy-4,5-dimethylphenyl)-4-methylhex-4-enoate
  参考文献：
  名称：

  Structure−Activity Relationships for Inhibition of Inosine Monophosphate Dehydrogenase by Nuclear Variants of Mycophenolic Acid

  摘要：

  Structure-activity relationships in the region of the phthalide ring of the inosine monophosphate dehydrogenase inhibitor mycophenolic acid have been explored. Replacement of the lactone ring with other cyclic moieties resulted in loss of potency, especially for larger groups. Replacement of the ring by acyclic substituents also indicated a strong sensitivity to steric bulk. A phenolic hydroxyl group, with an adjacent hydrogen bond acceptor, was found to be essential for high potency. The aromatic methyl group was essential for activity; the methoxyl group could be replaced by ethyl to give a compound with 2-4 times the potency of mycophenolic acid in vitro and in vivo.

  DOI：

  10.1021/jm9603633