6-chloro-4-((2-hydroxyethyl)(naphthalen-1-ylmethyl)amino)pyrimidin-2(1H)-one | 1403663-12-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 6-chloro-4-((2-hydroxyethyl)(naphthalen-1-ylmethyl)amino)pyrimidin-2(1H)-one
• 英文别名: 6-chloro-4-[2-hydroxyethyl(naphthalen-1-ylmethyl)amino]-1H-pyrimidin-2-one
• CAS: 1403663-12-6
• 化学式: C₁₇H₁₆ClN₃O₂
• 分子量: 329.786
• InChiKey: SYYZXXKVELXGBS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  64.9
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-甲基吗啉 、 6-chloro-4-((2-hydroxyethyl)(naphthalen-1-ylmethyl)amino)pyrimidin-2(1H)-one 以 N-甲基吡咯烷酮 为溶剂， 反应 0.5h， 生成 4-((2-hydroxyethyl)(naphthalen-1-ylmethyl)amino)-6-(2-methylmorpholino)pyrimidin-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
• 作为产物：
  描述：

  1-萘甲醛 在 三乙酰氧基硼氢化钠 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 24.0h， 生成 6-chloro-4-((2-hydroxyethyl)(naphthalen-1-ylmethyl)amino)pyrimidin-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