1-(4-Hydroxy-2,6-dimethylphenyl)-6-nitro-3,4-dihydroquinazolin-2-one | 678173-22-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 英文名称: 1-(4-Hydroxy-2,6-dimethylphenyl)-6-nitro-3,4-dihydroquinazolin-2-one
• CAS: 678173-22-3
• 化学式: C₁₆H₁₅N₃O₄
• 分子量: 313.313
• InChiKey: APVJUNCEEKSNBD-UHFFFAOYSA-N

物化性质

• 沸点：
  624.9±55.0 °C(Predicted)
• 密度：
  1.381±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  23
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  98.4
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-(4-Hydroxy-2,6-dimethylphenyl)-6-nitro-3,4-dihydroquinazolin-2-one 在 palladium on activated charcoal 氯磺酰异氰酸酯 、 氢气 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 32.0h， 生成 6-Amino-1-[2,6-dimethyl-4-(3-morpholin-4-yl-propoxy)-phenyl]-3,4-dihydro-1H-quinazolin-2-one
  参考文献：
  名称：

  A novel Pd-catalyzed cyclization reaction of ureas for the synthesis of dihydroquinazolinone p38 kinase inhibitors

  摘要：

  A series of potent p38 inhibitors based on the dihydroquinazoline scaffold was synthesized using a novel Pd-catalyzed cyclization reaction of aryl-benzyl ureas. Optimization of this compound class led to compound 20, which inhibits p38alpha in vitro with IC50 = 14 nM and is active in the mouse TNFalpha-release model. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2003.11.006
• 作为产物：
  描述：

  2-chloro-5-nitrobenzylamine 在 4-二甲氨基吡啶 、 potassium phosphate 、 tris-(dibenzylideneacetone)dipalladium(0) 、 2-(二环己基膦基)联苯 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 32.0h， 生成 1-(4-Hydroxy-2,6-dimethylphenyl)-6-nitro-3,4-dihydroquinazolin-2-one
  参考文献：
  名称：

  A novel Pd-catalyzed cyclization reaction of ureas for the synthesis of dihydroquinazolinone p38 kinase inhibitors

  摘要：

  A series of potent p38 inhibitors based on the dihydroquinazoline scaffold was synthesized using a novel Pd-catalyzed cyclization reaction of aryl-benzyl ureas. Optimization of this compound class led to compound 20, which inhibits p38alpha in vitro with IC50 = 14 nM and is active in the mouse TNFalpha-release model. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2003.11.006

文献信息

• A novel Pd-catalyzed cyclization reaction of ureas for the synthesis of dihydroquinazolinone p38 kinase inhibitors
  作者：Achim Schlapbach、Richard Heng、Franco Di Padova

  DOI：10.1016/j.bmcl.2003.11.006

  日期：2004.1

  A series of potent p38 inhibitors based on the dihydroquinazoline scaffold was synthesized using a novel Pd-catalyzed cyclization reaction of aryl-benzyl ureas. Optimization of this compound class led to compound 20, which inhibits p38alpha in vitro with IC50 = 14 nM and is active in the mouse TNFalpha-release model. (C) 2003 Elsevier Ltd. All rights reserved.