2-ethoxy-5-((4-propylpiperazin-1-yl)sulfonyl)nicotinic acid | 1147435-26-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 2-ethoxy-5-((4-propylpiperazin-1-yl)sulfonyl)nicotinic acid
• CAS: 1147435-26-4
• 化学式: C₁₅H₂₃N₃O₅S
• 分子量: 357.431
• InChiKey: SHUOQLGHTQNLIP-UHFFFAOYSA-N

物化性质

• 沸点：
  527.9±60.0 °C(predicted)
• 密度：
  1.294±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.89
• 重原子数：
  24.0
• 可旋转键数：
  7.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  100.04
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  4-氨基-5-乙基-1-甲基-1H-吡唑-3-羧酸酰胺 、 2-ethoxy-5-((4-propylpiperazin-1-yl)sulfonyl)nicotinic acid 在 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 N,N-二异丙基乙胺 作用下， 生成
  参考文献：
  名称：

  Highly potent and selective chiral inhibitors of PDE5: An illustration of Pfeiffer’s rule

  摘要：

  A series of potent chiral PDE5 inhibitors are described that are based on the sildenafil architecture but exhibit much greater selectivity over PDE6. Eudismic analysis of the SAR in this series provided a clear illustration of Pfeiffer's rule and indicated that the chiral motif was involved in a highly-stereoselective interaction with PDE5. This PDE5 specificity translated to levels of selectivity over PDE6 that were hitherto unprecedented in the sildenafil scaffold. UK-371,800 (compound 8) was identified as a development candidate from this series that married sildenafil-like molecular properties with high selectivity over PDE6. Clinical data confirm that UK-371,800 has markedly superior human pharmacokinetics to a previously-described higher molecular weight achiral analogue in this template (compound 1). (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2008.10.037