1,2-Dihydro-4-(3-iodophenylureido)-2-phenyl-1,2,4-triazolo[4,3-a]quinoxalin-1-one | 1040236-84-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 1,2-Dihydro-4-(3-iodophenylureido)-2-phenyl-1,2,4-triazolo[4,3-a]quinoxalin-1-one
• 英文别名: 1-(3-iodophenyl)-3-(1-oxo-2-phenyl-[1,2,4]triazolo[4,3-a]quinoxalin-4-yl)urea
• CAS: 1040236-84-7
• 化学式: C₂₂H₁₅IN₆O₂
• 分子量: 522.305
• InChiKey: DVZVMTRMOQLIJQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  31
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  89.4
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  3-碘苯异氰酸酯 、 4-Amino-2-phenyl-2H-[1,2,4]triazolo[4,3-a]quinoxalin-1-one 以 四氢呋喃 为溶剂， 反应 3.0h， 以95%的产率得到1,2-Dihydro-4-(3-iodophenylureido)-2-phenyl-1,2,4-triazolo[4,3-a]quinoxalin-1-one
  参考文献：
  名称：

  Synthesis, ligand–receptor modeling studies and pharmacological evaluation of novel 4-modified-2-aryl-1,2,4-triazolo[4,3-a]quinoxalin-1-one derivatives as potent and selective human A3 adenosine receptor antagonists

  摘要：

  The study of some 4-substituted-2-aryl-1,2,4-triazolo[4,3-a]quinoxalin-1-one derivatives, designed as hA(3) adenosine receptor antagonists, is reported. The new compounds bear on the four-position different acylamino, sulfonylamino, benzylureido and benzyloxy moieties, which have also been combined with a para-methoxy group on the 2-phenyl ring or with a nitro residue at the six-position. Many derivatives show high hA(3) adenosine receptor affinities and selectivities both versus hA(1) and hA(2A) receptors. The observed structure-affinity relationships of this class of antagonists have been exhaustively rationalized using the recently published ligand-based homology modeling (LBHM) approach. The selected 4-bismethanesulfonylamino-2-phenyl-1,2,4-triazolo[4,3a]quinoxalin-1-one (13), which shows high hA(3) affinity (K-i = 5.5 nM) and selectivity versus hA(1), hA(2A) (both selectivity ratios > 1800) and hA(2B) (cAMP assay, IC50 > 10,000 nM) receptors, was tested in an in vitro rat model of cerebral ischemia, proving to be effective in preventing the failure of synaptic activity, induced by oxygen and glucose deprivation in the hippocampus, and in delaying the occurrence of anoxic depolarization. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2008.04.039