5-<4-<2-ethoxy>phenylmethyl>thiazolidine-2,4-dione | 187340-70-1

• 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: 5-<4-<2-ethoxy>phenylmethyl>thiazolidine-2,4-dione
• 英文别名: 5-[4-[2-[N-(5-benzyloxy-2,3-dihydro-2,2,4,6,7-pentamethyl-1-benzofuran-3-ylmethyl)-N-methylamino]ethoxy]benzyl]thiazolidine-2,4-dione；5[4-[2-[N-(5-Benzyloxy-2,3-dihydro-2,2,4,6,7-pentamethyl-1-benzofuran-3-ylmethyl)-N-methylamino]ethoxy]benzyl]thiazolidine-2,4-dione；5-[[4-[2-[methyl-[(2,2,4,6,7-pentamethyl-5-phenylmethoxy-3H-1-benzofuran-3-yl)methyl]amino]ethoxy]phenyl]methyl]-1,3-thiazolidine-2,4-dione
• CAS: 187340-70-1
• 化学式: C₃₄H₄₀N₂O₅S
• 分子量: 588.768
• InChiKey: FXOUINVVVPKHFS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.7
• 重原子数：
  42
• 可旋转键数：
  11
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  102
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  5-<4-<2-ethoxy>phenylmethyl>thiazolidine-2,4-dione 生成 5-[4-[2-[N-(2,3-dihydro-5-hydroxy-2,2,4,6,7-pentamethyl-1-benzofuran-3-ylmethyl)-N-methylamino]ethoxy]benzyl]thiazolidine-2,4-dione
  参考文献：
  名称：

  Compounds having antidiabetic, hypolipidemic, antihypertensive

  摘要：

  已经制备出具有抗糖尿病、降血脂和降血压性质的吡唑烷二酮化合物（I）及其互变异构体、衍生物、立体异构体、多晶形态、药用盐、药用溶剂化合物和含有它们的药物组合物。

  公开号：

  US05925656A1
• 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 、 N,N-二甲基甲酰胺 、 苯 为溶剂， 反应 36.0h， 生成 5-<4-<2-ethoxy>phenylmethyl>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

文献信息

• Compounds having antidiabetic, hypolipidemic, antihypertensive
  申请人：Dr. Reddy's Research Foundation

  公开号：US05925656A1

  公开（公告）日：1999-07-20

  Thiazolidinediones of formula (I) their tautomeric forms, their derivatives, their stereoisomers, their polymorphs, their pharmaceutically acceptable salts, their pharmaceutically acceptable solvates and pharmaceutical compositions containing them having antidiabetic, hypolipidemic, and antihypertensive properties have been prepared. ##STR1##

  已经制备出具有抗糖尿病、降血脂和降血压性质的吡唑烷二酮化合物（I）及其互变异构体、衍生物、立体异构体、多晶形态、药用盐、药用溶剂化合物和含有它们的药物组合物。
• 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.