2-(4-morpholinyl)-6-(4-phenylmethoxyphenyl)-4H-pyran-4-one

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 2-(4-morpholinyl)-6-(4-phenylmethoxyphenyl)-4H-pyran-4-one
• 英文别名: 2-(4-morpholinyl)-6-(4-(phenylmethoxy)phenyl)-4H-pyran-4-one；2-(4-(benzyloxy)phenyl)-6-morpholino-4H-pyran-4-one；2-morpholin-4-yl-6-(4-phenylmethoxyphenyl)pyran-4-one
• 化学式: C₂₂H₂₁NO₄
• 分子量: 363.413
• InChiKey: QEXYPSGIECCYPS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  27
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  48
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  4-乙酰基吗啉 在 甲烷磺酸 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 正庚烷 、 乙基苯 为溶剂， 反应 7.5h， 生成 2-(4-morpholinyl)-6-(4-phenylmethoxyphenyl)-4H-pyran-4-one
  参考文献：
  名称：

  Synthesis of 2-Amino-6-phenyl-4H-pyran-4-ones

  摘要：

  一系列苯乙炔基β-酮酰胺与甲磺酸反应，高效地发生分子内环化，生成相应的2-氨基-6-苯基-4H-吡喃-4-酮。

  DOI：

  10.1055/s-1994-25402

文献信息

• Pyranone, Thiopyranone, and Pyridone Inhibitors of Phosphatidylinositol 3-Kinase Related Kinases. Structure−Activity Relationships for DNA-Dependent Protein Kinase Inhibition, and Identification of the First Potent and Selective Inhibitor of the Ataxia Telangiectasia Mutated Kinase
  作者：Jonathan J. Hollick、Laurent J. M. Rigoreau、Celine Cano-Soumillac、Xiaoling Cockcroft、Nicola J. Curtin、Mark Frigerio、Bernard T. Golding、Sophie Guiard、Ian R. Hardcastle、Ian Hickson、Marc G. Hummersone、Keith A. Menear、Niall M. B. Martin、Ian Matthews、David R. Newell、Rachel Ord、Caroline J. Richardson、Graeme C. M. Smith、Roger J. Griffin

  DOI：10.1021/jm061121y

  日期：2007.4.1

  Structure-activity relationships have been investigated for inhibition of DNA-dependent protein kinase (DNA-PK) and ATM kinase by a series of pyran-2-ones, pyran-4-ones, thiopyran-4-ones, and pyridin-4-ones. A wide range of IC50 values were observed for pyranones and thiopyranones substituted at the 6-position, with the 3- and 5-positions proving intolerant to substitution. Related pyran-2-ones, pyran-4-ones, and thiopyran-4-ones showed similar IC50 values against DNA-PK, whereas the pyridin-4-one system proved, in general, ineffective at inhibiting DNA-PK. Extended libraries exploring the 6-position of 2-morpholino-pyran-4-ones and 2-morpholino-thiopyrano-4-ones identified the first highly potent and selective ATM inhibitor 2-morpholin-4-yl-6-thianthren-1-yl-pyran-4-one (151C; ATM; IC50 = 13 nM) and revealed constrained SARs for ATM inhibition compared with DNA-PK. One of the most potent DNA-PK inhibitors identified, 2-(4-methoxyphenyl)-6-(morpholin-4-yl)pyran-4-one (16; DNA-PK; IC50 = 220 nM) effectively sensitized HeLa cells to the topoisomerase II inhibitor etoposide in vitro.
• ANTIATHEROSCLEROTIC AND ANTITHROMBOTIC 2-AMINO-6-PHENYL-4H-PYRAN-4-ONES
  申请人：THE UPJOHN COMPANY

  公开号：EP0489877B1

  公开（公告）日：1995-09-20
• US5252735A
  申请人：——

  公开号：US5252735A

  公开（公告）日：1993-10-12
• US5302613A
  申请人：——

  公开号：US5302613A

  公开（公告）日：1994-04-12
• [EN] ANTIATHEROSCLEROTIC AND ANTITHROMBOTIC 2-AMINO-6-PHENYL-4H-PYRAN-4-ONES
  申请人：——

  公开号：WO1992000290A1

  公开（公告）日：1992-01-09

  [EN] This invention relates to compounds of formula (I), which are useful as antiatherosclerotic agents and inhibitors of cell proliferation for the treatment of proliferative diseases. In addition, various compounds of formula (I) are useful inhibitors of platelet aggregation.
  [FR] Cette invention se rapporte à des composés de formule (I), utiles comme agents antiathérosclérotiques et inhibiteurs de prolifération de cellules dans le traitement de maladies prolifératrices. En outre, différents composés de formule (I) sont utiles comme antiagrégants plaquettaires.