5-[4-[2-[1-Oxo-1,2-dihydro-phthalazin-2-yl]ethoxy]phenyl methyl]thiazolidin-2,4-dione

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 英文名称: 5-[4-[2-[1-Oxo-1,2-dihydro-phthalazin-2-yl]ethoxy]phenyl methyl]thiazolidin-2,4-dione
• 英文别名: 5-[[4-[2-(1-Oxophthalazin-2-yl)ethoxy]phenyl]methyl]-1,3-thiazolidine-2,4-dione
• 化学式: C₂₀H₁₇N₃O₄S
• 分子量: 395.439
• InChiKey: PBXMWFFJGIWFGT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  28
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  113
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  1-(2H)-酞嗪酮 在 palladium on activated charcoal 哌啶 、 氢气 、 potassium carbonate 、 苯甲酸 作用下， 以 1,4-二氧六环 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 20.0~70.0 ℃ 、413.68 kPa 条件下， 反应 25.5h， 生成 5-[4-[2-[1-Oxo-1,2-dihydro-phthalazin-2-yl]ethoxy]phenyl methyl]thiazolidin-2,4-dione
  参考文献：
  名称：

  Novel phthalazinone and benzoxazinone containing thiazolidinediones as antidiabetic and hypolipidemic agents

  摘要：

  We report here the synthesis of a series of 5-[4-[2-[substituted phthalazinones-2(or 4)yl]ethoxy]phenylmethyl]thiazolidine-2,4-diones and 5-[4-[2-[2,3-benzoxazine-4-one-2-yl]ethoxy]phenylmethyl]thiazolidine-2,4-diones and their plasma glucose and plasma triglyceride lowering activity in db/db mice. In vitro PPAR gamma transactivation assay was performed in HEK 293T cells. In vitro and in vivo pharmacological studies showed that the phthalazinone analogue has better activity. PHT46 (compound 5a), the best compound in this series, showed better in vitro PPAR gamma transactivation potential than troglitazone and pioglitazone. In insulin resistant db/db mice, PHT46 showed better plasma glucose and triglyceride lowering activity than the standard drugs. Pharmacokinetic study in Wistar rats showed good systemic exposure of PHT46. Subchronic toxicity study in Wistar rats did not show any treatment-related adverse effect. (C) 2001 Editions scientifiques et medicales Elsevier SAS.

  DOI：

  10.1016/s0223-5234(01)01257-0

文献信息

• Heterocyclic compounds having antidiabetic hypolipidemic
  申请人：Dr. Reddy's Research Foundation

  公开号：US06011036A1

  公开（公告）日：2000-01-04

  The present invention relates to novel antidiabetic compounds, their tautomeric forms, their analogues, their derivatives, their stereoisomers, their polymorphs, their pharmaceutically acceptable salts, their pharmaceutically acceptable solvates and pharmaceutically acceptable compositions containing them. This invention particularly relates to novel azolidinedione compounds of the general formula (I), and their analogues, their derivatives, their tautomeric forms, their stereoisomers, their polymorphs, their pharmaceutically acceptable salts, pharmaceutically acceptable solvates and pharmaceutical compositions containing them. ##STR1##

  本发明涉及新型抗糖尿病化合物，它们的互变异构体、类似物、衍生物、立体异构体、多晶形态、药用可接受盐、药用可接受溶剂和含有它们的药用可接受组合物。本发明特别涉及一般式（I）的新型噁唑烷二酮化合物及其类似物、衍生物、互变异构体、立体异构体、多晶形态、药用可接受盐、药用可接受溶剂和含有它们的药用组合物。
• THIAZOLIDINEDIONE AND OXAZOLIDINEDIONE DERIVATIVES HAVING ANTIDIABETIC, HYPOLIPIDAEMIC AND ANTIHYPERTENSIVE PROPERTIES
  申请人：DR. REDDY'S RESEARCH FOUNDATION

  公开号：EP0971917A1

  公开（公告）日：2000-01-19
• US6011036A
  申请人：——

  公开号：US6011036A

  公开（公告）日：2000-01-04
• [EN] THIAZOLIDINEDIONE AND OXAZOLIDINEDIONE DERIVATIVES HAVING ANTIDIABETIC, HYPOLIPIDAEMIC AND ANTIHYPERTENSIVE PROPERTIES<br/>[FR] DERIVES DE THIAZOLIDINEDIONE ET D'OXAZOLIDINEDIONE AYANT DES PROPRIETES ANTIDIABETIQUES, HYPOLIPIDEMIQUES ET ANTIHYPERTENSEURS
  申请人：DR. REDDY'S RESEARCH FOUNDATION

  公开号：WO1998045292A1

  公开（公告）日：1998-10-15

  (EN) The present invention relates to novel antidiabetic compounds, their tautomeric forms, their analogues, their derivatives, their stereoisomers, their polymorphs, their pharmaceutically acceptable salts, their pharmaceutically acceptable solvates and pharmaceutically acceptable compositions containing them. This invention particularly relates to novel azolidinedione compounds of general formula (I), and their analogues, their derivatives, their tautomeric forms, their stereoisomers, their polymorphs, their pharmaceutically acceptable salts, pharmaceutically acceptable solvates and pharmaceutical compositions containing them.(FR) L'invention concerne des nouveaux composés antidiabétiques, leurs formes tautomères, leurs analogues, leurs dérivés, leurs stéréoisomères, leurs polymorphes, leurs sels pharmaceutiquement acceptables, leurs solvats pharmaceutiquement acceptables et des composition pharmaceutiquement acceptables les contenant. Elle porte notamment sur des nouveaux composés azolidinedione de formule générale (I) et leurs analogues, leurs dérivés, leur formes tautomères, leurs stéréoisomères, leurs polymorphes, leurs sels pharmaceutiquement acceptables, leurs solvats pharmaceutiquement acceptables et des compositions pharmaceutiques les contenant.
• Novel phthalazinone and benzoxazinone containing thiazolidinediones as antidiabetic and hypolipidemic agents
  作者：Gurram R Madhavan、Ranjan Chakrabarti、Sunil K.B Kumar、Parimal Misra、Rao N.V.S Mamidi、V Balraju、Katneni Kasiram、Ravi K Babu、Juluri Suresh、Braj B Lohray

  DOI：10.1016/s0223-5234(01)01257-0

  日期：2001.8

  We report here the synthesis of a series of 5-[4-[2-[substituted phthalazinones-2(or 4)yl]ethoxy]phenylmethyl]thiazolidine-2,4-diones and 5-[4-[2-[2,3-benzoxazine-4-one-2-yl]ethoxy]phenylmethyl]thiazolidine-2,4-diones and their plasma glucose and plasma triglyceride lowering activity in db/db mice. In vitro PPAR gamma transactivation assay was performed in HEK 293T cells. In vitro and in vivo pharmacological studies showed that the phthalazinone analogue has better activity. PHT46 (compound 5a), the best compound in this series, showed better in vitro PPAR gamma transactivation potential than troglitazone and pioglitazone. In insulin resistant db/db mice, PHT46 showed better plasma glucose and triglyceride lowering activity than the standard drugs. Pharmacokinetic study in Wistar rats showed good systemic exposure of PHT46. Subchronic toxicity study in Wistar rats did not show any treatment-related adverse effect. (C) 2001 Editions scientifiques et medicales Elsevier SAS.