N-[4-(1-Allyl-3-butyl-2,6-dioxo-2,3,6,7-tetrahydro-1H-purin-8-yl)-phenyl]-acetamide | 628279-03-8

• 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: N-[4-(1-Allyl-3-butyl-2,6-dioxo-2,3,6,7-tetrahydro-1H-purin-8-yl)-phenyl]-acetamide
• 英文别名: N-[4-[3-Butyl-2,3,6,9-tetrahydro-2,6-dioxo-1-(2-propen-1-yl)-1H-purin-8-yl]phenyl]acetamide；N-[4-(3-butyl-2,6-dioxo-1-prop-2-enyl-7H-purin-8-yl)phenyl]acetamide
• CAS: 628279-03-8
• 化学式: C₂₀H₂₃N₅O₃
• 分子量: 381.434
• InChiKey: UUWRLRBZDQIEFS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  28
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  98.4
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  对乙酰氨基苯甲酸 在 咪唑 、 sodium hydroxide 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 甲醇 为溶剂， 生成 N-[4-(1-Allyl-3-butyl-2,6-dioxo-2,3,6,7-tetrahydro-1H-purin-8-yl)-phenyl]-acetamide
  参考文献：
  名称：

  Modified 3-Alkyl-1,8-dibenzylxanthines as GTP-Competitive inhibitors of phosphoenolpyruvate carboxykinase

  摘要：

  The first non-substrate like inhibitors of human cytosolic phosphoenolpyruvate carboxykinase (PEPCK) competitive with GTP are reported. An effort to discover orally active compounds that improve glucose homeostasis in Type 2 diabetics by reversibly inhibiting PEPCK led to the discovery of 1-allyl-3-butyl-8-methylxanthine (5). We now report modifications at N-1 and C-8 that improved the in vitro activity of the initial xanthine HTS hit by 100-fold and a developing SAR for this class of inhibitor. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(03)00722-4