4’-去甲基-6’-对甲苯磺酰基霉酚酸 | 171808-03-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 4’-去甲基-6’-对甲苯磺酰基霉酚酸
• 英文名称: (E) 6-(1,3-dihydro-6-hydroxy-7-methyl-3-oxo-4-p-toluenesulfonyloxyisobenzofuran-5-yl)-4-methyl-4-hexenoic acid
• 英文别名: 4'-Desmethyl-6'-tosylmycophenolic Acid；(E)-6-[6-hydroxy-7-methyl-4-(4-methylphenyl)sulfonyloxy-3-oxo-1H-2-benzofuran-5-yl]-4-methylhex-4-enoic acid
• CAS: 171808-03-0
• 化学式: C₂₃H₂₄O₈S
• 分子量: 460.505
• InChiKey: ATGXPGLZKZKOOJ-MKMNVTDBSA-N

物化性质

• 溶解度：
  溶于二氯甲烷

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  32
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  136
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  4’-去甲基-6’-对甲苯磺酰基霉酚酸 在 吡啶 、 四(三苯基膦)钯 、 对甲苯磺酸 作用下， 以 1,4-二氧六环 、 二氯甲烷 为溶剂， 反应 138.25h， 生成 methyl (E)-6-(6-cyano-4-hydroxy-7-methyl-3-oxo-1H-2-benzofuran-5-yl)-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
• 作为产物：
  描述：

  霉酚酸 在 2,3,5-三甲基吡啶 、 4-二甲氨基吡啶 、 对甲苯磺酸 、 三乙胺 、 lithium iodide 作用下， 以 二氯甲烷 为溶剂， 反应 36.5h， 生成 4’-去甲基-6’-对甲苯磺酰基霉酚酸
  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

文献信息

• 6-substituted mycophenolic acid and derivatives
  申请人：Syntex (U.S.A.) Inc.

  公开号：US05444072A1

  公开（公告）日：1995-08-22

  The disclosed 6-substituted derivatives of mycophenolic acid are therapeutic agents advantageous in the treatment of disease states indicated for mycophenolic acid and/or mycophenolate mofetil.

  所披露的6-取代衍生物是治疗剂，在治疗适用于麦考酚酸和/或麦考酚酯酶的疾病状态中具有优势。
• Method of using 4-amino 6-substituted mycophenolic acid and derivatives
  申请人：Syntex (U.S.A.) Inc.

  公开号：US05525602A1

  公开（公告）日：1996-06-11

  The disclosed derivatives of mycophenolic acid are therapeutic agents advantageous in the treatment of disease states indicated for mycophenolic acid and/or mycophenolate mofetil and other immunosuppressant agents.

  所披露的霉酚酸衍生物是治疗疾病状态中的治疗剂，适用于霉酚酸和/或麻酮酯酸酯以及其他免疫抑制剂。
• 4-AMINO 6-SUBSTITUTED MYCOPHENOLIC ACID AND DERIVATIVES WITH IMMUNOSUPPRESSIVE ACTIVITY
  申请人：Syntex (U.S.A.) LLC

  公开号：EP0745071B1

  公开（公告）日：2001-12-05
• 6-SUBSTITUTED MYCOPHENOLIC AND DERIVATIVES WITH IMMUNOSUPPRESSIVE ACTIVITY
  申请人：Syntex (U.S.A.) LLC

  公开号：EP0745075B1

  公开（公告）日：2001-12-05
• US5444072A
  申请人：——

  公开号：US5444072A

  公开（公告）日：1995-08-22