6-((2-hydroxypropyl)(naphthalen-1-ylmethyl)amino)-4-morpholinopyrimidin-2(1H)-one | 1403663-04-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 6-((2-hydroxypropyl)(naphthalen-1-ylmethyl)amino)-4-morpholinopyrimidin-2(1H)-one
• 英文别名: 6-[2-hydroxypropyl(naphthalen-1-ylmethyl)amino]-4-morpholin-4-yl-1H-pyrimidin-2-one
• CAS: 1403663-04-6
• 化学式: C₂₂H₂₆N₄O₃
• 分子量: 394.473
• InChiKey: ITYRDLOSIWZNFA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  29
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  77.4
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  1-((Naphthalen-1-ylmethyl)amino)propan-2-ol 以 N-甲基吡咯烷酮 为溶剂， 反应 0.75h， 生成 6-((2-hydroxypropyl)(naphthalen-1-ylmethyl)amino)-4-morpholinopyrimidin-2(1H)-one
  参考文献：
  名称：

  Discovery of phosphoinositide 3-kinases (PI3K) p110β isoform inhibitor 4-[2-hydroxyethyl(1-naphthylmethyl)amino]-6-[(2S)-2-methylmorpholin-4-yl]-1H-pyrimidin-2-one, an effective antithrombotic agent without associated bleeding and insulin resistance

  摘要：

  Structure-based evolution of the original fragment leads resulted in the identification of 4-[2-hydroxyethyl(1-naphthylmethyl)amino]-6-[(2S)-2-methylmorpholin-4-yl]-1H-pyrimidin-2-one, (S)-21, a potent, selective phosphoinositide 3-kinases (PI3K) p110 beta isoform inhibitor with favourable in vivo antiplatelet effect. Despite its antiplatelet action, (S)-21 did not significantly increase bleeding time in dogs. Additionally, due to its enhanced selectivity over p110 alpha, (S)-21 did not induce any insulin resistance in rats. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.08.102

文献信息

• Discovery of phosphoinositide 3-kinases (PI3K) p110β isoform inhibitor 4-[2-hydroxyethyl(1-naphthylmethyl)amino]-6-[(2S)-2-methylmorpholin-4-yl]-1H-pyrimidin-2-one, an effective antithrombotic agent without associated bleeding and insulin resistance
  作者：Fabrizio Giordanetto、Andreas Wållberg、Saswati Ghosal、Tommy Iliefski、Johan Cassel、Zhong-Qing Yuan、Henrik von Wachenfeldt、Søren M. Andersen、Tord Inghardt、Anders Tunek、Sven Nylander

  DOI：10.1016/j.bmcl.2012.08.102

  日期：2012.11

  Structure-based evolution of the original fragment leads resulted in the identification of 4-[2-hydroxyethyl(1-naphthylmethyl)amino]-6-[(2S)-2-methylmorpholin-4-yl]-1H-pyrimidin-2-one, (S)-21, a potent, selective phosphoinositide 3-kinases (PI3K) p110 beta isoform inhibitor with favourable in vivo antiplatelet effect. Despite its antiplatelet action, (S)-21 did not significantly increase bleeding time in dogs. Additionally, due to its enhanced selectivity over p110 alpha, (S)-21 did not induce any insulin resistance in rats. (C) 2012 Elsevier Ltd. All rights reserved.