rosiglitazone potassium salt

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: rosiglitazone potassium salt
• 英文别名: 5-[4-[2-(N-methyl-N-(2-pyridyl)amino)ethoxy]benzyl]thiazolidine-2,4-dione potassium salt；5-[[4-[2-(methyl-2-pyridinylamino)ethoxy]phenyl]methyl]-2,4-thiazolidinedione potassium salt；Potassium;5-[[4-[2-[methyl(pyridin-2-yl)amino]ethoxy]phenyl]methyl]-4-oxo-1,3-thiazol-2-olate
• 化学式: C₁₈H₁₈N₃O₃S*K
• 分子量: 395.524
• InChiKey: RWOGCLSZSSKLEN-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  0.28
• 重原子数：
  26
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  85.8
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  rosiglitazone potassium salt 在 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 、 三氟乙酸 、 sodium iodide 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 (E)-2-methoxy-4-[3-(4-(nitrooxy)butoxy)-3-oxoprop-1-en-1-yl]phenyl [(5-(4-(2-(methyl(pyridin-2-yl)amino)ethoxy)benzyl)-2,4-dioxo-3-thiazolidinyl)methyl]succinate
  参考文献：
  名称：

  Design and synthesis of rosiglitazone-ferulic acid-nitric oxide donor trihybrids for improving glucose tolerance

  摘要：

  Glucose intolerance is associated with metabolic syndrome and type 2 diabetes mellitus (T2DM) while some new therapeutic drugs, such as rosiglitazone (Rosi), for T2DM can cause severe cardiovascular side effects. Herein we report the synthesis of Rosi-ferulic acid (FA)-nitric oxide (NO) donor trihybrids to improve glucose tolerance and minimize the side effects. In comparison with Rosi, the most active compound 21 exhibited better effects on improving glucose tolerance, which was associated with its NO production, antioxidant and anti-inflammatory activities. Furthermore, 21 displayed relatively high stability in the simulated gastrointestinal environments and human liver microsomes, and released Rosi in plasma. More importantly, 21, unlike Rosi, had little stimulatory effect on the membrane translocation of aquaporin-2 (AQP2) in kidney collecting duct epithelial cells. These, together with a better safety profile, suggest that the trihybrids, like 21, may be promising candidates for intervention of glucose intolerance-related metabolic syndrome and T2DM. (C) 2018 Published by Elsevier Masson SAS.

  DOI：

  10.1016/j.ejmech.2018.10.006

文献信息

• [EN] INCLUSION COMPLEXES OF ROSIGLITAZONE<br/>[FR] NOUVEAUX COMPOSES
  申请人：——

  公开号：WO2003099337A3

  公开（公告）日：2004-02-26
• Design and synthesis of rosiglitazone-ferulic acid-nitric oxide donor trihybrids for improving glucose tolerance
  作者：Jingchao Liu、Zhangjian Huang、Wenhuan Ma、Sixun Peng、Yunman Li、Katrina M. Miranda、Jide Tian、Yihua Zhang

  DOI：10.1016/j.ejmech.2018.10.006

  日期：2019.1

  Glucose intolerance is associated with metabolic syndrome and type 2 diabetes mellitus (T2DM) while some new therapeutic drugs, such as rosiglitazone (Rosi), for T2DM can cause severe cardiovascular side effects. Herein we report the synthesis of Rosi-ferulic acid (FA)-nitric oxide (NO) donor trihybrids to improve glucose tolerance and minimize the side effects. In comparison with Rosi, the most active compound 21 exhibited better effects on improving glucose tolerance, which was associated with its NO production, antioxidant and anti-inflammatory activities. Furthermore, 21 displayed relatively high stability in the simulated gastrointestinal environments and human liver microsomes, and released Rosi in plasma. More importantly, 21, unlike Rosi, had little stimulatory effect on the membrane translocation of aquaporin-2 (AQP2) in kidney collecting duct epithelial cells. These, together with a better safety profile, suggest that the trihybrids, like 21, may be promising candidates for intervention of glucose intolerance-related metabolic syndrome and T2DM. (C) 2018 Published by Elsevier Masson SAS.