7-ethyl-1-(4-methoxybenzyl)-3-methyl-8-(4-(2-(methyl(pyridin-2-yl)amino) ethoxy)phenyl)-1H-purine-2,6(3H,7H)-dione

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并嘧啶类
• 英文名称: 7-ethyl-1-(4-methoxybenzyl)-3-methyl-8-(4-(2-(methyl(pyridin-2-yl)amino) ethoxy)phenyl)-1H-purine-2,6(3H,7H)-dione
• 英文别名: 7-Ethyl-1-[(4-methoxyphenyl)methyl]-3-methyl-8-[4-[2-[methyl(pyridin-2-yl)amino]ethoxy]phenyl]purine-2,6-dione；7-ethyl-1-[(4-methoxyphenyl)methyl]-3-methyl-8-[4-[2-[methyl(pyridin-2-yl)amino]ethoxy]phenyl]purine-2,6-dione
• 化学式: C₃₀H₃₂N₆O₄
• 分子量: 540.622
• InChiKey: AQISDTMMSWHAOI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  40
• 可旋转键数：
  10
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  93
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  6-氨基-1-甲基尿嘧啶 在 ammonium hydroxide 、 sodium dithionite 、 sodium hydride 、 potassium carbonate 、 溶剂黄146 、 sodium nitrite 作用下， 以 甲醇 、 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 24.58h， 生成 7-ethyl-1-(4-methoxybenzyl)-3-methyl-8-(4-(2-(methyl(pyridin-2-yl)amino) ethoxy)phenyl)-1H-purine-2,6(3H,7H)-dione
  参考文献：
  名称：

  Synthesis and lipid-lowering evaluation of 3-methyl-1H-purine-2,6-dione derivatives as potent and orally available anti-obesity agents

  摘要：

  Obesity accompanied with metabolic disorder is often complicated with a strong link of dyslipidemia and insulin resistance, whose indicator is the excess accumulation of triglycerides (TG) in cells. Consideration the idea of lipid-lowering and improving insulin resistance, 34 novel compounds by combination the xanthine scaffold with the chain of Rosiglitazone have been synthesized. Among them, several compounds showed efficiency on reducing TG in 3T3-L1 adipoctyes, and 11c exhibited the most optimal capacity in lipid-lowering and improving obese clinical symptoms in DIO mice. Furthermore, the hydrochloride of 11c (11c center dot HCl) showed excellent bioavailability, 58.94%, over 2 folds than that (28.03%) of 11c, and the anti-obesity effect of 11c center dot HCl at 50 mg/kg dose was better than that of Metjormin at 150 mg/kg dose in DIO mice, almost reversed HFD to a normal level. Thus, 11c center dot HCl might be a potent and orally available anti-obesity agent via alleviating the obese clinical symptoms, body fat, improving serum parameters and insulin resistance and TG clearance in liver. (c) 2014 Published by Elsevier Masson SAS.

  DOI：

  10.1016/j.ejmech.2014.09.094

文献信息

• Synthesis and lipid-lowering evaluation of 3-methyl-1H-purine-2,6-dione derivatives as potent and orally available anti-obesity agents
  作者：Linhong He、Heying Pei、Liang Ma、Yuzhi Pu、Jinying Chen、Zhuowei Liu、Yan Ran、Lei Lei、Suhong Fu、Minghai Tang、Aihua Peng、Chaofeng Long、Lijuan Chen

  DOI：10.1016/j.ejmech.2014.09.094

  日期：2014.11

  Obesity accompanied with metabolic disorder is often complicated with a strong link of dyslipidemia and insulin resistance, whose indicator is the excess accumulation of triglycerides (TG) in cells. Consideration the idea of lipid-lowering and improving insulin resistance, 34 novel compounds by combination the xanthine scaffold with the chain of Rosiglitazone have been synthesized. Among them, several compounds showed efficiency on reducing TG in 3T3-L1 adipoctyes, and 11c exhibited the most optimal capacity in lipid-lowering and improving obese clinical symptoms in DIO mice. Furthermore, the hydrochloride of 11c (11c center dot HCl) showed excellent bioavailability, 58.94%, over 2 folds than that (28.03%) of 11c, and the anti-obesity effect of 11c center dot HCl at 50 mg/kg dose was better than that of Metjormin at 150 mg/kg dose in DIO mice, almost reversed HFD to a normal level. Thus, 11c center dot HCl might be a potent and orally available anti-obesity agent via alleviating the obese clinical symptoms, body fat, improving serum parameters and insulin resistance and TG clearance in liver. (c) 2014 Published by Elsevier Masson SAS.