1-[2,6-Dimethyl-4-(3-morpholin-4-ylpropoxy)phenyl]-6-nitro-3,4-dihydroquinazolin-2-one | 678173-28-9

• 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-[2,6-Dimethyl-4-(3-morpholin-4-ylpropoxy)phenyl]-6-nitro-3,4-dihydroquinazolin-2-one
• CAS: 678173-28-9
• 化学式: C₂₃H₂₈N₄O₅
• 分子量: 440.499
• InChiKey: FHIMXKODERDATB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  32
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  99.9
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  1-[2,6-Dimethyl-4-(3-morpholin-4-ylpropoxy)phenyl]-6-nitro-3,4-dihydroquinazolin-2-one 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 反应 16.0h， 以98%的产率得到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：

  1-(4-(t-butyldimethylsilanoxy)-2,6-dimethylphenyl)-3-(2-chloro-5-nitrobenzyl)urea 在 potassium phosphate 、 tris-(dibenzylideneacetone)dipalladium(0) 、 氯磺酰异氰酸酯 、 2-(二环己基膦基)联苯 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 32.0h， 生成 1-[2,6-Dimethyl-4-(3-morpholin-4-ylpropoxy)phenyl]-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.