4-(5-benzyloxy-2,2,4,6,7-pentamethyl-1-benzofuran-3-ylmethoxy)benzaldehyde | 224953-99-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 香豆素
• 英文名称: 4-(5-benzyloxy-2,2,4,6,7-pentamethyl-1-benzofuran-3-ylmethoxy)benzaldehyde
• 英文别名: 4-[(2,2,4,6,7-pentamethyl-5-phenylmethoxy-3H-1-benzofuran-3-yl)methoxy]benzaldehyde
• CAS: 224953-99-5
• 化学式: C₂₈H₃₀O₄
• 分子量: 430.544
• InChiKey: YVVJZRXWBQTMBR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6
• 重原子数：
  32
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-(5-benzyloxy-2,2,4,6,7-pentamethyl-1-benzofuran-3-ylmethoxy)benzaldehyde 在 盐酸 、 哌啶鎓苯甲酸盐 作用下， 以 溶剂黄146 、 甲苯 为溶剂， 反应 3.5h， 生成 (5Z)-5-[[4-[(5-hydroxy-2,2,4,6,7-pentamethyl-3H-1-benzofuran-3-yl)methoxy]phenyl]methylidene]-1,3-thiazolidine-2,4-dione
  参考文献：
  名称：

  Novel Antidiabetic and Hypolipidemic Agents. 3. Benzofuran-Containing Thiazolidinediones

  摘要：

  Several thiazolidinedione derivatives having 5-hydroxy-2,3-dihydro-2,2,4,6,7-pentamethylbenzofuran moieties and their 5-benzyloxy derivatives and 5-hydroxy-2,4,6,7-tetramethylbenzofuran moieties were synthesized and evaluated in db/db mice. Insertion of an N-Me group into the linker between thiazolidinedione and substituted benzofuran pharmacophores showed considerable improvement in their euglycemic activity. Further improvement has been observed when a pyrrolidine moiety is introduced in the structure to give 5-[4-[N-[3(R/S)-5-benzyloxy-2,3-dihydro-2,2,4,6,7-pentamethylbenzofuran-3-ylmethyl]-(2S)-pyrrolidin-2-ylmethoxy]phenylene]-thiazolidine-2,4-dione (21a). At a 100 mg/kg/day dose of the maleate salt, compound 21a reduced the plasma glucose and triglyceride to the level of lean littermate, i.e. 8 +/- 1 mM, and is the most potent and efficacious compound reported in this series.

  DOI：

  10.1021/jm980549x
• 作为产物：
  描述：

  5-benzyloxy-2,2,4,6,7-pentamethyl-1-benzofuran-3-carbinol 在 potassium carbonate 、 三乙胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 15.0h， 生成 4-(5-benzyloxy-2,2,4,6,7-pentamethyl-1-benzofuran-3-ylmethoxy)benzaldehyde
  参考文献：
  名称：

  Novel Antidiabetic and Hypolipidemic Agents. 3. Benzofuran-Containing Thiazolidinediones

  摘要：

  Several thiazolidinedione derivatives having 5-hydroxy-2,3-dihydro-2,2,4,6,7-pentamethylbenzofuran moieties and their 5-benzyloxy derivatives and 5-hydroxy-2,4,6,7-tetramethylbenzofuran moieties were synthesized and evaluated in db/db mice. Insertion of an N-Me group into the linker between thiazolidinedione and substituted benzofuran pharmacophores showed considerable improvement in their euglycemic activity. Further improvement has been observed when a pyrrolidine moiety is introduced in the structure to give 5-[4-[N-[3(R/S)-5-benzyloxy-2,3-dihydro-2,2,4,6,7-pentamethylbenzofuran-3-ylmethyl]-(2S)-pyrrolidin-2-ylmethoxy]phenylene]-thiazolidine-2,4-dione (21a). At a 100 mg/kg/day dose of the maleate salt, compound 21a reduced the plasma glucose and triglyceride to the level of lean littermate, i.e. 8 +/- 1 mM, and is the most potent and efficacious compound reported in this series.

  DOI：

  10.1021/jm980549x

文献信息

• Novel Antidiabetic and Hypolipidemic Agents. 3. Benzofuran-Containing Thiazolidinediones
  作者：K. Anji Reddy、B. B. Lohray、V. Bhushan、A. C. Bajji、K. Vivekananda Reddy、P. Rajamohan Reddy、T. Hari Krishna、I. Nageswara Rao、H. Kumar Jajoo、N. V. S. Mamidi Rao、Ranjan Chakrabarti、T. Dileepkumar、R. Rajagopalan

  DOI：10.1021/jm980549x

  日期：1999.6.1

  Several thiazolidinedione derivatives having 5-hydroxy-2,3-dihydro-2,2,4,6,7-pentamethylbenzofuran moieties and their 5-benzyloxy derivatives and 5-hydroxy-2,4,6,7-tetramethylbenzofuran moieties were synthesized and evaluated in db/db mice. Insertion of an N-Me group into the linker between thiazolidinedione and substituted benzofuran pharmacophores showed considerable improvement in their euglycemic activity. Further improvement has been observed when a pyrrolidine moiety is introduced in the structure to give 5-[4-[N-[3(R/S)-5-benzyloxy-2,3-dihydro-2,2,4,6,7-pentamethylbenzofuran-3-ylmethyl]-(2S)-pyrrolidin-2-ylmethoxy]phenylene]-thiazolidine-2,4-dione (21a). At a 100 mg/kg/day dose of the maleate salt, compound 21a reduced the plasma glucose and triglyceride to the level of lean littermate, i.e. 8 +/- 1 mM, and is the most potent and efficacious compound reported in this series.