4-[2-[N-(5-benzyloxy-2,3-dihydro-2,2,4,6,7-pentamethyl-1-benzofuran-3-ylmethyl)-N-methylamino]ethoxy]benzaldehyde | 187341-22-6

• 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-[2-[N-(5-benzyloxy-2,3-dihydro-2,2,4,6,7-pentamethyl-1-benzofuran-3-ylmethyl)-N-methylamino]ethoxy]benzaldehyde
• 英文别名: 4-<2-ethoxy>benzaldehyde；4-[2-[methyl-[(2,2,4,6,7-pentamethyl-5-phenylmethoxy-3H-1-benzofuran-3-yl)methyl]amino]ethoxy]benzaldehyde
• CAS: 187341-22-6
• 化学式: C₃₁H₃₇NO₄
• 分子量: 487.639
• InChiKey: LOZUHMCAORNHMZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.1
• 重原子数：
  36
• 可旋转键数：
  10
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  48
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4-[2-[N-(5-benzyloxy-2,3-dihydro-2,2,4,6,7-pentamethyl-1-benzofuran-3-ylmethyl)-N-methylamino]ethoxy]benzaldehyde 生成 5-[4-[2-[N-(5-benzyloxy-2,3-dihydro-2,2,4,6,7-pentamethyl-1-benzofuran-3-ylmethyl)-N-methylamino]ethoxy]phenyl methylene]thiazolidine-2,4-dione
  参考文献：
  名称：

  Thiazolidinedione derivatives having antidiabetic, hypolipidaemic, antihypertensive properties, process for their preparation and pharmaceutical compositions containing them

  摘要：

  公开号：

  EP0801063B1
• 作为产物：
  描述：

  5-benzyloxy-2,2,4,6,7-pentamethyl-1-benzofuran-3-carbinol 在 氯化亚砜 、 sodium hydride 、 三乙胺 作用下， 以 二氯甲烷 、 苯 为溶剂， 反应 48.5h， 生成 4-[2-[N-(5-benzyloxy-2,3-dihydro-2,2,4,6,7-pentamethyl-1-benzofuran-3-ylmethyl)-N-methylamino]ethoxy]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

• Thiazolidinedione derivatives having antidiabetic, hypolipidaemic antihypertensive properties, process for their preparation and pharmaceutical compositions containing them
  申请人：DR. REDDY'S RESEARCH FOUNDATION

  公开号：EP0801063A1

  公开（公告）日：1997-10-15

  A compound of the general formula (I), where A represents, substituted or unsunstituted unsaturated aliphatic, alicyclic, aromatic, heterocyclic groups, B represents a substituted or unsubstituted divalent alkylene or alkenyl group having 1 to 10 carbon atoms, wherein substituents may be present in one or more of the divalent alkylene or alkenyl groups, D represents a substituted or insubstituted divalent alkenyl, alkynyl, aralkyl alkoxycarbonyl or aryloxycarbonyl groups, X represents CH2, C=O, CH-OH, sulphur, oxygen, N-Y, where Y represents hydrogen, substituted or unsubstituted alkyl, aryl, aralkyl or acyl, Ar represents a divalent aromatic, single or fused ring system, with or without substituents, the ring may contain one or more hetero atoms selected from nitrogen, sulphur, or oxygen; R1 and R2 each represents hydrogen or together represent a bond either or both may be substituents or both together form a part of a ring. Methods for preparing the compound and pharmaceutical compositions containing a compound of formula (I).

  通式(I)的化合物、 其中 A 代表取代或未取代的不饱和脂肪族、脂环族、芳香族、杂环族基团，B 代表具有 1 至 10 个碳原子的取代或未取代的二价亚烷基或烯基，其中取代基可存在于一个或多个二价亚烷基或烯基之中，D 代表取代或未取代的二价烯基、炔基、芳烷基烷氧基羰基或芳氧基羰基，X 代表 CH2、C=O、CH-OH、硫、氧、烷氧基羰基、芳烷氧基羰基或芳氧基羰基、X代表CH2、C＝O、CH-OH、硫、氧、N-Y，其中Y代表氢、取代或未取代的烷基、芳基、芳烷基或酰基，Ar代表二价芳香族、单环或熔合环体系，带或不带取代基，环中可含有一个或多个选自氮、硫或氧的杂原子；R1 和 R2 各自代表氢，或共同代表键，或两者均为取代基，或两者共同构成环的一部分。制备化合物和含有式（I）化合物的药物组合物的方法。
• Thiazolidinedione derivatives having antidiabetic, hypolipidaemic, antihypertensive properties, process for their preparation and pharmaceutical compositions containing them
  申请人：Dr. Reddy's Laboratories Ltd.

  公开号：EP0801063B1

  公开（公告）日：2003-01-15
• 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.