4-[6-(Methylamino)-3-pyridyl]-8-(1-methylpyrazol-4-yl)-1-(2-tetrahydrofuran-2-ylethyl)benzofuro[3,2-d]pyrimidin-2-one | 1431433-71-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: 4-[6-(Methylamino)-3-pyridyl]-8-(1-methylpyrazol-4-yl)-1-(2-tetrahydrofuran-2-ylethyl)benzofuro[3,2-d]pyrimidin-2-one
• 英文别名: 4-[6-(methylamino)pyridin-3-yl]-8-(1-methylpyrazol-4-yl)-1-[2-(oxolan-2-yl)ethyl]-[1]benzofuro[3,2-d]pyrimidin-2-one
• CAS: 1431433-71-4
• 化学式: C₂₆H₂₆N₆O₃
• 分子量: 470.531
• InChiKey: FNIVQLRCXVGJSR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  35
• 可旋转键数：
  6
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  97.8
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  Ethyl-5-bromo-3-ethoxycarbonylamino-1-benzofuran-2-carboxylate 在 (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride 、 正丁基锂 、 水 、 potassium carbonate 、 caesium carbonate 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 二甲基亚砜 为溶剂， 生成 4-[6-(Methylamino)-3-pyridyl]-8-(1-methylpyrazol-4-yl)-1-(2-tetrahydrofuran-2-ylethyl)benzofuro[3,2-d]pyrimidin-2-one
  参考文献：
  名称：

  Nucleotide competing reverse transcriptase inhibitors: Discovery of a series of non-basic benzofurano[3,2-d]pyrimidin-2-one derived inhibitors

  摘要：

  A HTS screen led to the identification of a benzofurano[3,2-d]pyrimidin-2-one core structure which upon further optimization resulted in 1 as a potent HIV-1 nucleotide competing reverse transcriptase inhibitor (NcRTI). Investigation of the SAR at N-1 allowed significant improvements in potency and when combined with the incorporation of heterocycles at C-8 resulted in potent analogues not requiring a basic amine to achieve antiviral activity. Additional modifications at N-1 resulted in 33 which demonstrated excellent antiviral potency and improved physicochemical properties. (C) 2013 Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmcl.2013.02.021

文献信息

• Nucleotide competing reverse transcriptase inhibitors: Discovery of a series of non-basic benzofurano[3,2-d]pyrimidin-2-one derived inhibitors
  作者：Clint A. James、Patrick DeRoy、Martin Duplessis、Paul J. Edwards、Teddy Halmos、Joannie Minville、Louis Morency、Sébastien Morin、Bruno Simoneau、Martin Tremblay、Richard Bethell、Michael Cordingley、Jianmin Duan、Louie Lamorte、Alex Pelletier、Daniel Rajotte、Patrick Salois、Sonia Tremblay、Claudio F. Sturino

  DOI：10.1016/j.bmcl.2013.02.021

  日期：2013.5

  A HTS screen led to the identification of a benzofurano[3,2-d]pyrimidin-2-one core structure which upon further optimization resulted in 1 as a potent HIV-1 nucleotide competing reverse transcriptase inhibitor (NcRTI). Investigation of the SAR at N-1 allowed significant improvements in potency and when combined with the incorporation of heterocycles at C-8 resulted in potent analogues not requiring a basic amine to achieve antiviral activity. Additional modifications at N-1 resulted in 33 which demonstrated excellent antiviral potency and improved physicochemical properties. (C) 2013 Published by Elsevier Ltd.