N-(5-chloro-6-quinolin-3-yloxypyridin-3-yl)-3-fluorobenzenesulfonamide | 1416131-53-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: N-(5-chloro-6-quinolin-3-yloxypyridin-3-yl)-3-fluorobenzenesulfonamide
• CAS: 1416131-53-7
• 化学式: C₂₀H₁₃ClFN₃O₃S
• 分子量: 429.859
• InChiKey: ZXYMDJFNJBHIOR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  29
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  89.6
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  2-羟基-5-硝基吡啶 在 吡啶 、 喹啉 、 盐酸 、 tin(II) chloride dihdyrate 、 caesium carbonate 、 三氯氧磷 作用下， 以 二氯甲烷 、 乙酸乙酯 、 N,N-二甲基甲酰胺 为溶剂， 反应 11.5h， 生成 N-(5-chloro-6-quinolin-3-yloxypyridin-3-yl)-3-fluorobenzenesulfonamide
  参考文献：
  名称：

  Synthesis of N-(5-chloro-6-(quinolin-3-yloxy)pyridin-3-yl)benzenesulfonamide derivatives as non-TZD peroxisome proliferator-activated receptor γ (PPARγ) agonist

  摘要：

  The thiazolidinediones (TZDs) are a class of oral antidiabetic drugs that improve insulin sensitivity in patients with type 2 diabetes. Although the mechanism by which the TZDs lower insulin resistance is unclear, they are known to target the peroxisome proliferator-activated receptor gamma (PPAR gamma), a nuclear hormone receptor. Ligands for PPAR gamma regulate adipocyte production and secretion of fatty acids as well as glucose metabolism, resulting in increased insulin sensitivity in adipose tissue, liver, and skeletal muscle. However, TZDs have several adverse effects, including weight gain and liver toxicity. Herein we report identification of non-TZD PPAR gamma agonists which exhibit beneficial effects similar to that of TZDs in animal models, but without the associated adverse effects. (C) 2012 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2012.10.027

文献信息

• Synthesis of N-(5-chloro-6-(quinolin-3-yloxy)pyridin-3-yl)benzenesulfonamide derivatives as non-TZD peroxisome proliferator-activated receptor γ (PPARγ) agonist
  作者：Swapnil Bajare、Jessy Anthony、Amrutha Nair、Rosalind Marita、Anagha Damre、Dharmeshkumar Patel、Chandrika Rao、H. Sivaramakrishnan、Nabajyoti Deka

  DOI：10.1016/j.ejmech.2012.10.027

  日期：2012.12

  The thiazolidinediones (TZDs) are a class of oral antidiabetic drugs that improve insulin sensitivity in patients with type 2 diabetes. Although the mechanism by which the TZDs lower insulin resistance is unclear, they are known to target the peroxisome proliferator-activated receptor gamma (PPAR gamma), a nuclear hormone receptor. Ligands for PPAR gamma regulate adipocyte production and secretion of fatty acids as well as glucose metabolism, resulting in increased insulin sensitivity in adipose tissue, liver, and skeletal muscle. However, TZDs have several adverse effects, including weight gain and liver toxicity. Herein we report identification of non-TZD PPAR gamma agonists which exhibit beneficial effects similar to that of TZDs in animal models, but without the associated adverse effects. (C) 2012 Elsevier Masson SAS. All rights reserved.