ethyl {4-[(Z)-(2,4-dioxo-1,3-thiazolidin-5-ylidene)methyl]phenoxy}acetate | 1430399-26-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: ethyl {4-[(Z)-(2,4-dioxo-1,3-thiazolidin-5-ylidene)methyl]phenoxy}acetate
• 英文别名: ethyl 2-[4-[(Z)-(2,4-dioxo-1,3-thiazolidin-5-ylidene)methyl]phenoxy]acetate
• CAS: 1430399-26-0
• 化学式: C₁₄H₁₃NO₅S
• 分子量: 307.327
• InChiKey: DGPRJJLHBMETII-XFFZJAGNSA-N

物化性质

• 密度：
  1.384±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  107
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  对羟基苯甲醛 在 哌啶 、 potassium carbonate 、 苯甲酸 作用下， 以 丙酮 、 甲苯 为溶剂， 反应 6.5h， 生成 ethyl {4-[(Z)-(2,4-dioxo-1,3-thiazolidin-5-ylidene)methyl]phenoxy}acetate
  参考文献：
  名称：

  Discovery of Thiazolidine-2,4-Dione/Biphenylcarbonitrile Hybrid as Dual PPAR α/γ Modulator with Antidiabetic Effect:In vitro, In SilicoandIn VivoApproaches

  摘要：

  A small series of thiazolidine‐2,4‐dione and barbituric acid derivatives 1–4 was prepared using a short synthetic route, and all compounds were characterized by elemental analysis, mass spectrometry, and NMR (1H, 13C) spectroscopy. Their in vitro relative expression of peroxisome proliferator‐activated receptor &agr1; and peroxisome proliferator‐activated receptor &ggr1; was evaluated. Compound 1 showed an increase in the mRNA expression of both peroxisome proliferator‐activated receptor isoforms, as well as the GLUT‐4 levels. The antidiabetic activity of compound 1 was determined at 50 mg/kg single dose using a non‐insulin‐dependent diabetes mellitus rat model. The results indicated a significant decrease in plasma glucose levels. Additionally, we performed a molecular docking of compound 1 into the ligand binding pocket of peroxisome proliferator‐activated receptor &agr1; and peroxisome proliferator‐activated receptor &ggr1;. In these binding models, compound 1 may bind into the active site of both isoforms showing important short contacts with the peroxisome proliferator‐activated receptor &ggr1; residues: Tyr 473, His 449, Ser 289, His 323; and peroxisome proliferator‐activated receptor α residues: Tyr 464, His 440, Ser 280 and Tyr 314.

  DOI：

  10.1111/cbdd.12102

文献信息

• [EN] AN IMPROVED PROCESS FOR THE PREPARATION OF THIAZOLIDINE-2,4-DIONE DERIVATIVES<br/>[FR] PROCEDE AMELIORE DE PREPARATION DE DERIVES DE THIAZOLIDINE-2,4-DIONE
  申请人：REDDY RESEARCH FOUNDATION

  公开号：WO2000015638A1

  公开（公告）日：2000-03-23

  An improved process for the preparation of 5-[4-[[3-Methyl- 4-oxo-3,4- dihydroquinazolin -2-yl]methoxy] benzyl] thiazolidine -2,4-dione of formula (1) which comprises: reducing the compound of formula (2') where R represents a (C1-C4)alkyl group using Raney Nickel or Magnesium in alcohol having 1 to 4 carbon atoms or mixtures thereof, if desired reesterifying using sufphuric acid at a temperature in the range of 0 °C to 60 °C to obtain a compound of formula (3') wherein R is as defined above, hydrolyzing the compound of formula (3') wherein R is as defined above, by conventional methods to obtain the acid of formula (4), condensing the acid of formula (4) with N-methyl anthranilamide directly without any preactivation of the acid to produce the compound of formula (1) and if desired, converting the compound of formula (1) to pharmaceutically acceptable salts thereof by conventional methods.

  一种改进的制备5-[4-[[3-甲基-4-氧代-3,4-二氢喹唑啉-2-基]甲氧基]苯甲基]噻唑烷-2,4-二酮的方法，其包括：使用Raney镍或镁在具有1至4个碳原子的醇或其混合物中还原式（2'）化合物，其中R代表（C1-C4）烷基，如果需要，使用硫酸在0℃至60℃的温度下重新酯化以获得式（3'）化合物，其中R如上所定义，通过传统方法水解式（3'）化合物，以获得式（4）的酸，将式（4）的酸与N-甲基蒽酰胺直接缩合，而无需预激活酸，以产生式（1）的化合物，如果需要，通过传统方法将式（1）的化合物转化为药学上可接受的盐。
• AN IMPROVED PROCESS FOR THE PREPARATION OF THIAZOLIDINE-2,4-DIONE DERIVATIVES
  申请人：DR. REDDY'S RESEARCH FOUNDATION

  公开号：EP1114047A1

  公开（公告）日：2001-07-11
• US6469167B1
  申请人：——

  公开号：US6469167B1

  公开（公告）日：2002-10-22
• Discovery of Thiazolidine-2,4-Dione/Biphenylcarbonitrile Hybrid as Dual PPAR α/γ Modulator with Antidiabetic Effect:<i>In vitro, In Silico</i>and<i>In Vivo</i>Approaches
  作者：Sergio Hidalgo-Figueroa、Juan J. Ramírez-Espinosa、Samuel Estrada-Soto、Julio C. Almanza-Pérez、Rubén Román-Ramos、Francisco J. Alarcón-Aguilar、Jesús V. Hernández-Rosado、Hermenegilda Moreno-Díaz、Daniel Díaz-Coutiño、Gabriel Navarrete-Vázquez

  DOI：10.1111/cbdd.12102

  日期：2013.4

  A small series of thiazolidine‐2,4‐dione and barbituric acid derivatives 1–4 was prepared using a short synthetic route, and all compounds were characterized by elemental analysis, mass spectrometry, and NMR (1H, 13C) spectroscopy. Their in vitro relative expression of peroxisome proliferator‐activated receptor &agr1; and peroxisome proliferator‐activated receptor &ggr1; was evaluated. Compound 1 showed an increase in the mRNA expression of both peroxisome proliferator‐activated receptor isoforms, as well as the GLUT‐4 levels. The antidiabetic activity of compound 1 was determined at 50 mg/kg single dose using a non‐insulin‐dependent diabetes mellitus rat model. The results indicated a significant decrease in plasma glucose levels. Additionally, we performed a molecular docking of compound 1 into the ligand binding pocket of peroxisome proliferator‐activated receptor &agr1; and peroxisome proliferator‐activated receptor &ggr1;. In these binding models, compound 1 may bind into the active site of both isoforms showing important short contacts with the peroxisome proliferator‐activated receptor &ggr1; residues: Tyr 473, His 449, Ser 289, His 323; and peroxisome proliferator‐activated receptor α residues: Tyr 464, His 440, Ser 280 and Tyr 314.