2-(4-Acetamidophenyl)-N-[6-amino-1-butyl-3-(3-fluorobenzyl)-2,4-dioxo-1,2,3,4-tetrahydro-5-pyrimidinyl]acetamide | 628279-20-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-(4-Acetamidophenyl)-N-[6-amino-1-butyl-3-(3-fluorobenzyl)-2,4-dioxo-1,2,3,4-tetrahydro-5-pyrimidinyl]acetamide
• 英文别名: 2-(4-acetamidophenyl)-N-[6-amino-1-butyl-3-[(3-fluorophenyl)methyl]-2,4-dioxopyrimidin-5-yl]acetamide
• CAS: 628279-20-9
• 化学式: C₂₅H₂₈FN₅O₄
• 分子量: 481.527
• InChiKey: RFHNNJPISDNNQT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  35
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  125
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2-(4-Acetamidophenyl)-N-[6-amino-1-butyl-3-(3-fluorobenzyl)-2,4-dioxo-1,2,3,4-tetrahydro-5-pyrimidinyl]acetamide 在 sodium hydroxide 作用下， 以 甲醇 为溶剂， 生成 N-{4-[3-butyl-1-(3-fluoro-benzyl)-2,6-dioxo-2,3,6,7-tetrahydro-1H-purin-8-ylmethyl]-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
• 作为产物：
  描述：

  6-Amino-1-butyl-3-(3-fluoro-benzyl)-1H-pyrimidine-2,4-dione 在 咪唑 、 溶剂黄146 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 sodium nitrite 作用下， 生成 2-(4-Acetamidophenyl)-N-[6-amino-1-butyl-3-(3-fluorobenzyl)-2,4-dioxo-1,2,3,4-tetrahydro-5-pyrimidinyl]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

文献信息

• Modified 3-Alkyl-1,8-dibenzylxanthines as GTP-Competitive inhibitors of phosphoenolpyruvate carboxykinase
  作者：Louise H. Foley、Ping Wang、Pete Dunten、Gwendolyn Ramsey、Mary-Lou Gubler、Stanley J. Wertheimer

  DOI：10.1016/s0960-894x(03)00722-4

  日期：2003.10

  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.