2-(5-(2-ethoxyphenyl)-7-oxo-3-phenyl-6,7-dihydro-1H-pyrazolo[4,3-d]pyrimidin-1-yl)acetamide | 1370409-66-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 2-(5-(2-ethoxyphenyl)-7-oxo-3-phenyl-6,7-dihydro-1H-pyrazolo[4,3-d]pyrimidin-1-yl)acetamide
• 英文别名: 2-[5-(2-ethoxyphenyl)-7-oxo-3-phenyl-6H-pyrazolo[4,3-d]pyrimidin-1-yl]acetamide
• CAS: 1370409-66-7
• 化学式: C₂₁H₁₉N₅O₃
• 分子量: 389.414
• InChiKey: MCIIAOGKTNLVDX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  29
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  112
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  2-乙氧基苯甲酸 在 氨 、 sodium ethanolate 、 sodium hydride 、 三乙胺 、 bromo-tris(1-pyrrolidinyl)phosphonium hexafluorophosphate 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 乙醇 、 metal oil 、 水 、 1,2-二氯乙烷 为溶剂， 反应 73.0h， 生成 2-(5-(2-ethoxyphenyl)-7-oxo-3-phenyl-6,7-dihydro-1H-pyrazolo[4,3-d]pyrimidin-1-yl)acetamide
  参考文献：
  名称：

  Synthesis and evaluation of human phosphodiesterases (PDE) 5 inhibitor analogs as trypanosomal PDE inhibitors. Part 1. Sildenafil analogs

  摘要：

  Parasitic diseases, such as African sleeping sickness, have a significant impact on the health and wellbeing in the poorest regions of the world. Pragmatic drug discovery efforts are needed to find new therapeutic agents. In this Letter we describe target repurposing efforts focused on trypanosomal phosphodiesterases. We outline the synthesis and biological evaluation of analogs of sildenafil (1), a human PDE5 inhibitor, for activities against trypanosomal PDEB1 (TbrPDEB1). We find that, while low potency analogs can be prepared, this chemical class is a sub-optimal starting point for further development of TbrPDE inhibitors. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.01.119

文献信息

• Synthesis and evaluation of human phosphodiesterases (PDE) 5 inhibitor analogs as trypanosomal PDE inhibitors. Part 1. Sildenafil analogs
  作者：Cuihua Wang、Trent D. Ashton、Alden Gustafson、Nicholas D. Bland、Stefan O. Ochiana、Robert K. Campbell、Michael P. Pollastri

  DOI：10.1016/j.bmcl.2012.01.119

  日期：2012.4

  Parasitic diseases, such as African sleeping sickness, have a significant impact on the health and wellbeing in the poorest regions of the world. Pragmatic drug discovery efforts are needed to find new therapeutic agents. In this Letter we describe target repurposing efforts focused on trypanosomal phosphodiesterases. We outline the synthesis and biological evaluation of analogs of sildenafil (1), a human PDE5 inhibitor, for activities against trypanosomal PDEB1 (TbrPDEB1). We find that, while low potency analogs can be prepared, this chemical class is a sub-optimal starting point for further development of TbrPDE inhibitors. (C) 2012 Elsevier Ltd. All rights reserved.