methyl 6-({2-[4-(aminosulfonyl)phenyl]ethyl}amino)-4-oxo-1,3-diphenyl-2-thioxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate | 1166242-02-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: methyl 6-({2-[4-(aminosulfonyl)phenyl]ethyl}amino)-4-oxo-1,3-diphenyl-2-thioxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate
• 英文别名: Methyl 4-oxo-1,3-diphenyl-6-[2-(4-sulfamoylphenyl)ethylamino]-2-sulfanylidenepyrimidine-5-carboxylate
• CAS: 1166242-02-9
• 化学式: C₂₆H₂₄N₄O₅S₂
• 分子量: 536.632
• InChiKey: IVZXRINVYCVDJL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  37
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  163
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  methyl 6-(methylthio)-4-oxo-1,3-diphenyl-2-thioxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate 、 4-(2-氨乙基)苯磺酰胺 以 N,N-二甲基甲酰胺 为溶剂， 反应 6.0h， 以82%的产率得到methyl 6-({2-[4-(aminosulfonyl)phenyl]ethyl}amino)-4-oxo-1,3-diphenyl-2-thioxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate
  参考文献：
  名称：

  6-Amino-4-oxo-1,3-diphenyl-2-thioxo-1,2,3,4-tetrahydropyrimidine-5-carbonyl derivatives as a new class of potent inhibitors of Interleukin-8-induced neutrophil chemotaxis

  摘要：

  A series of 6-amino-4-oxo-1,3-diphenyl-2-thioxo-1,2,3,4-tetrahydropyrimidine-5-carbonyl derivatives was synthesized. The compounds demonstrated to be novel, potent and selective inhibitors of Interleukin-8-induced human neutrophil chemotaxis. A SAR study was performed by varying the carbonyl function at position 5 and the chain linked to the amino group at position 6 of the scaffold. All the compounds of the series displayed inhibitory activity at nano- or picomolar concentrations against Interleukin-8-driven migration and no activity against fMLP- and C5a-induced chemotaxis. The binding tests of selected compounds on CXCR1 and CXCR2 receptors were negative. The most potent derivative showed in vivo efficacy in a mouse model of Zymosan-induced peritonitis. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2009.04.006

文献信息

• 6-Amino-4-oxo-1,3-diphenyl-2-thioxo-1,2,3,4-tetrahydropyrimidine-5-carbonyl derivatives as a new class of potent inhibitors of Interleukin-8-induced neutrophil chemotaxis
  作者：Sara Cesarini、Andrea Spallarossa、Angelo Ranise、Olga Bruno、Nicoletta Arduino、Maria Bertolotto、Franco Dallegri、Massimiliano Tognolini、Thomas Gobbetti、Elisabetta Barocelli

  DOI：10.1016/j.bmc.2009.04.006

  日期：2009.5

  A series of 6-amino-4-oxo-1,3-diphenyl-2-thioxo-1,2,3,4-tetrahydropyrimidine-5-carbonyl derivatives was synthesized. The compounds demonstrated to be novel, potent and selective inhibitors of Interleukin-8-induced human neutrophil chemotaxis. A SAR study was performed by varying the carbonyl function at position 5 and the chain linked to the amino group at position 6 of the scaffold. All the compounds of the series displayed inhibitory activity at nano- or picomolar concentrations against Interleukin-8-driven migration and no activity against fMLP- and C5a-induced chemotaxis. The binding tests of selected compounds on CXCR1 and CXCR2 receptors were negative. The most potent derivative showed in vivo efficacy in a mouse model of Zymosan-induced peritonitis. (C) 2009 Elsevier Ltd. All rights reserved.