6-Amino-1-[2,6-dimethyl-4-(3-morpholin-4-yl-propoxy)-phenyl]-3,4-dihydro-1H-quinazolin-2-one | 678173-29-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 6-Amino-1-[2,6-dimethyl-4-(3-morpholin-4-yl-propoxy)-phenyl]-3,4-dihydro-1H-quinazolin-2-one
• CAS: 678173-29-0
• 化学式: C₂₃H₃₀N₄O₃
• 分子量: 410.516
• InChiKey: PRSFCUAJICOQKO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.35
• 重原子数：
  30.0
• 可旋转键数：
  6.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  80.06
• 氢给体数：
  2.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  3-氯-4-氟苯磺酰氯 、 6-Amino-1-[2,6-dimethyl-4-(3-morpholin-4-yl-propoxy)-phenyl]-3,4-dihydro-1H-quinazolin-2-one 在 吡啶 、 4-二甲氨基吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 16.0h， 以27%的产率得到3-chloro-N-[1-[2,6-dimethyl-4-(3-morpholin-4-ylpropoxy)phenyl]-2-oxo-3,4-dihydroquinazolin-6-yl]-4-fluorobenzenesulfonamide
  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 palladium on activated charcoal 4-二甲氨基吡啶 、 potassium phosphate 、 tris-(dibenzylideneacetone)dipalladium(0) 、 氯磺酰异氰酸酯 、 氢气 、 2-(二环己基膦基)联苯 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 64.0h， 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