(3-(1-(1-benzylpiperidin-4-yl)-4-morpholino-1H-pyrazolo[3,4-d]pyrimidin-6-yl)phenyl)methanol | 1208243-82-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: (3-(1-(1-benzylpiperidin-4-yl)-4-morpholino-1H-pyrazolo[3,4-d]pyrimidin-6-yl)phenyl)methanol
• 英文别名: [3-[1-(1-benzylpiperidin-4-yl)-4-morpholin-4-ylpyrazolo[3,4-d]pyrimidin-6-yl]phenyl]methanol
• CAS: 1208243-82-6
• 化学式: C₂₈H₃₂N₆O₂
• 分子量: 484.601
• InChiKey: ADGMDJYORUZUNO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  36
• 可旋转键数：
  6
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  79.5
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (3-(1-(1-benzylpiperidin-4-yl)-4-morpholino-1H-pyrazolo[3,4-d]pyrimidin-6-yl)phenyl)methanol 在 palladium 10% on activated carbon 、 氢气 作用下， 以 甲醇 为溶剂， 生成 [3-(4-Morpholin-4-yl-1-piperidin-4-ylpyrazolo[3,4-d]pyrimidin-6-yl)phenyl]methanol
  参考文献：
  名称：

  Novel purine and pyrazolo[3,4-d]pyrimidine inhibitors of PI3 kinase-α: Hit to lead studies

  摘要：

  Series of purine and pyrazolo[3,4-d] pyrimidine inhibitors of phosphatidylinositol-3-kinases (PI3K) have been prepared. The optimized purine inhibitors show good potency in a PI3K p110 alpha (PI3K-alpha) fluorescence polarization assay with good selectivity versus PI3K p110 gamma (PI3K-gamma) and the mammalian target of rapamycin (mTOR). The related pyrazolo[3,4-d]pyrimidines show potent PI3K-alpha and mTOR inhibition with good selectivity versus PI3K-gamma. Representative compounds showed activity in a cellular proliferation assay against Caco-2 colorectal, LoVo colorectal and PC3MM2 prostate adenocarcinoma cancer cells. Signaling through the PI3K pathway was confirmed via inhibition of phospho-AKT in MDA-361 cells. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.11.051
• 作为产物：
  描述：

  4-(1-(1-benzylpiperidin-4-yl)-6-chloro-1H-pyrazolo[3,4-d]pyrimidin-4-yl)morpholine 、 3-羟甲基苯硼酸 在 四(三苯基膦)钯 、 sodium carbonate 作用下， 以 1,4-二氧六环 、 水 为溶剂， 生成 (3-(1-(1-benzylpiperidin-4-yl)-4-morpholino-1H-pyrazolo[3,4-d]pyrimidin-6-yl)phenyl)methanol
  参考文献：
  名称：

  Novel purine and pyrazolo[3,4-d]pyrimidine inhibitors of PI3 kinase-α: Hit to lead studies

  摘要：

  Series of purine and pyrazolo[3,4-d] pyrimidine inhibitors of phosphatidylinositol-3-kinases (PI3K) have been prepared. The optimized purine inhibitors show good potency in a PI3K p110 alpha (PI3K-alpha) fluorescence polarization assay with good selectivity versus PI3K p110 gamma (PI3K-gamma) and the mammalian target of rapamycin (mTOR). The related pyrazolo[3,4-d]pyrimidines show potent PI3K-alpha and mTOR inhibition with good selectivity versus PI3K-gamma. Representative compounds showed activity in a cellular proliferation assay against Caco-2 colorectal, LoVo colorectal and PC3MM2 prostate adenocarcinoma cancer cells. Signaling through the PI3K pathway was confirmed via inhibition of phospho-AKT in MDA-361 cells. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.11.051

文献信息

• Novel purine and pyrazolo[3,4-d]pyrimidine inhibitors of PI3 kinase-α: Hit to lead studies
  作者：Adam M. Gilbert、Pawel Nowak、Natasja Brooijmans、Matthew G. Bursavich、Christoph Dehnhardt、Efren Delos Santos、Larry R. Feldberg、Irwin Hollander、Stephen Kim、Sabrina Lombardi、Kaapjoo Park、Aranapakam M. Venkatesan、Robert Mallon

  DOI：10.1016/j.bmcl.2009.11.051

  日期：2010.1

  Series of purine and pyrazolo[3,4-d] pyrimidine inhibitors of phosphatidylinositol-3-kinases (PI3K) have been prepared. The optimized purine inhibitors show good potency in a PI3K p110 alpha (PI3K-alpha) fluorescence polarization assay with good selectivity versus PI3K p110 gamma (PI3K-gamma) and the mammalian target of rapamycin (mTOR). The related pyrazolo[3,4-d]pyrimidines show potent PI3K-alpha and mTOR inhibition with good selectivity versus PI3K-gamma. Representative compounds showed activity in a cellular proliferation assay against Caco-2 colorectal, LoVo colorectal and PC3MM2 prostate adenocarcinoma cancer cells. Signaling through the PI3K pathway was confirmed via inhibition of phospho-AKT in MDA-361 cells. (C) 2009 Elsevier Ltd. All rights reserved.