5-[2-{(5-phenyl-1,3,4-oxadiazol-2-yl)methoxy}benzylidene]thiazolidine-2,4-dione

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 5-[2-{(5-phenyl-1,3,4-oxadiazol-2-yl)methoxy}benzylidene]thiazolidine-2,4-dione
• 化学式: C₁₉H₁₃N₃O₄S
• 分子量: 379.396
• InChiKey: UYRUEQWFFAEGFR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.64
• 重原子数：
  27.0
• 可旋转键数：
  5.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  94.32
• 氢给体数：
  1.0
• 氢受体数：
  7.0

反应信息

• 作为产物：
  描述：

  2-甲酰苯氧乙酸 在 sodium hydroxide 、 三氯氧磷 作用下， 以 乙醇 为溶剂， 生成 5-[2-{(5-phenyl-1,3,4-oxadiazol-2-yl)methoxy}benzylidene]thiazolidine-2,4-dione
  参考文献：
  名称：

  Design, synthesis, in silico molecular docking and biological evaluation of novel oxadiazole based thiazolidine-2,4-diones bis-heterocycles as PPAR-γ agonists

  摘要：

  A library of novel 1,3,4-oxadiazole and 2-4-thiazolidinedione based bis-heterocycles 7 (a-r) has been synthesized which exhibited significant PPAR-gamma transactivation and blood glucose lowering effect comparable with the standard drugs Pioglitazone and Rosiglitazone. Compounds 7m and 7r did not cause body weight gain and were found to be free from hepatotoxic and cardiotoxic side effects. Compounds 7m and 7r increased PPAR-gamma gene expression by 2.10 and 2.00 folds, respectively in comparison to the standard drugs Pioglitazone (1.5 fold) and Rosiglitazone (1.0 fold). Therefore the compounds 7m and 7r may be considered as potential candidates for development of new antidiabetic agents. (C) 2014 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2014.09.010

文献信息

• Design, synthesis, in silico molecular docking and biological evaluation of novel oxadiazole based thiazolidine-2,4-diones bis-heterocycles as PPAR-γ agonists
  作者：Syed Nazreen、Mohammad Sarwar Alam、Hinna Hamid、Mohammad Shahar Yar、Syed Shafi、Abhijeet Dhulap、Perwez Alam、M.A.Q. Pasha、Sameena Bano、Mohammad Mahboob Alam、Saqlain Haider、Yakub Ali、Chetna Kharbanda、K.K. Pillai

  DOI：10.1016/j.ejmech.2014.09.010

  日期：2014.11

  A library of novel 1,3,4-oxadiazole and 2-4-thiazolidinedione based bis-heterocycles 7 (a-r) has been synthesized which exhibited significant PPAR-gamma transactivation and blood glucose lowering effect comparable with the standard drugs Pioglitazone and Rosiglitazone. Compounds 7m and 7r did not cause body weight gain and were found to be free from hepatotoxic and cardiotoxic side effects. Compounds 7m and 7r increased PPAR-gamma gene expression by 2.10 and 2.00 folds, respectively in comparison to the standard drugs Pioglitazone (1.5 fold) and Rosiglitazone (1.0 fold). Therefore the compounds 7m and 7r may be considered as potential candidates for development of new antidiabetic agents. (C) 2014 Elsevier Masson SAS. All rights reserved.