8-Chloro-1-(3-methoxypropyl)-4-(4-piperazin-1-ylphenyl)benzofuro[3,2-d]pyrimidin-2-one | 1431433-55-4

• 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: 8-Chloro-1-(3-methoxypropyl)-4-(4-piperazin-1-ylphenyl)benzofuro[3,2-d]pyrimidin-2-one
• 英文别名: 8-chloro-1-(3-methoxypropyl)-4-(4-piperazin-1-ylphenyl)-[1]benzofuro[3,2-d]pyrimidin-2-one
• CAS: 1431433-55-4
• 化学式: C₂₄H₂₅ClN₄O₃
• 分子量: 452.941
• InChiKey: DACVHXDVQONGAV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  32
• 可旋转键数：
  6
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  70.3
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  ethyl N-[2-(4-bromobenzoyl)-5-chloro-1-benzofuran-3-yl]carbamate 在 ammonium acetate 、 palladium diacetate 、 caesium carbonate 、 2-(二叔丁基膦)联苯 、 sodium t-butanolate 作用下， 以 二甲基亚砜 、 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 生成 8-Chloro-1-(3-methoxypropyl)-4-(4-piperazin-1-ylphenyl)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.