N-[3-(4-methoxyphenyl)1-phenyl-1H-1,2,4-triazol-5-yl]benzamide

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: N-[3-(4-methoxyphenyl)1-phenyl-1H-1,2,4-triazol-5-yl]benzamide
• 英文别名: N-[5-(4-methoxyphenyl)-2-phenyl-1,2,4-triazol-3-yl]benzamide
• 化学式: C₂₂H₁₈N₄O₂
• 分子量: 370.411
• InChiKey: ZYLUZUXPUFXKNB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  28
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  69
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  4-methoxy-N'-phenylbenzohydrazonoyl chloride 在 吡啶 作用下， 以 四氢呋喃 为溶剂， 反应 25.33h， 生成 N-benzoyl-N-[3-(4-methoxyphenyl)-1-phenyl-1H-1,2,4-triazol-5-yl]benzamide 、 N-[3-(4-methoxyphenyl)1-phenyl-1H-1,2,4-triazol-5-yl]benzamide
  参考文献：
  名称：

  1,2,4-Triazolo[1,5-a]quinoxaline derivatives and their simplified analogues as adenosine A3 receptor antagonists. Synthesis, structure–affinity relationships and molecular modeling studies

  摘要：

  The 1,2,4-triazolo[1,5-a]quinoxaline (TQX) scaffold was extensively investigated in our previously reported studies and recently, our attention was focused at position 5 of the tricyclic nucleus where different acyl and carboxylate moieties were introduced (compounds 2-15). This study produced some interesting compounds endowed with good hA(3) receptor affinity and selectivity. In addition, to find new insights about the structural requirements for hA(3) receptor-ligand interaction, the tricyclic TQX ring was destroyed yielding some 1,2,4-triazole derivatives (compounds 16-23). These simplified compounds, though maintaining the crucial structural requirements for adenosine receptor-ligand interaction, have a very low hA(3) adenosine receptor affinity, the only exception being compound 23 (1-[3-(4-methoxyphenyl)-1-phenyl-1H-1,2,4-triazol-5-yl]-3-phenylurea) endowed with a K-i value in the micro-molar range and high hA(3) selectivity versus both hA(1) and hA(2A) AR subtypes. Evaluation of the side products obtained in the herein reported synthetic pathways led to the identification of some new triazolo[1,5-a]quinoxalines as hA(3)AR antagonists (compounds 24-27). These derivatives, though lacking the classical structural requirements for the anchoring at the hA(3) receptor site, show high hA(3) affinity and in some case selectivity versus hA(1) and hA(2A) subtypes. Molecular docking of the herein reported tricyclic and simplified derivatives was carried out to depict their hypothetical binding mode to our model of hA(3) receptor. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2014.11.033

文献信息

• 1,2,4-Triazolo[1,5-a]quinoxaline derivatives and their simplified analogues as adenosine A3 receptor antagonists. Synthesis, structure–affinity relationships and molecular modeling studies
  作者：Daniela Catarzi、Flavia Varano、Daniela Poli、Lucia Squarcialupi、Marco Betti、Letizia Trincavelli、Claudia Martini、Diego Dal Ben、Ajiroghene Thomas、Rosaria Volpini、Vittoria Colotta

  DOI：10.1016/j.bmc.2014.11.033

  日期：2015.1

  The 1,2,4-triazolo[1,5-a]quinoxaline (TQX) scaffold was extensively investigated in our previously reported studies and recently, our attention was focused at position 5 of the tricyclic nucleus where different acyl and carboxylate moieties were introduced (compounds 2-15). This study produced some interesting compounds endowed with good hA(3) receptor affinity and selectivity. In addition, to find new insights about the structural requirements for hA(3) receptor-ligand interaction, the tricyclic TQX ring was destroyed yielding some 1,2,4-triazole derivatives (compounds 16-23). These simplified compounds, though maintaining the crucial structural requirements for adenosine receptor-ligand interaction, have a very low hA(3) adenosine receptor affinity, the only exception being compound 23 (1-[3-(4-methoxyphenyl)-1-phenyl-1H-1,2,4-triazol-5-yl]-3-phenylurea) endowed with a K-i value in the micro-molar range and high hA(3) selectivity versus both hA(1) and hA(2A) AR subtypes. Evaluation of the side products obtained in the herein reported synthetic pathways led to the identification of some new triazolo[1,5-a]quinoxalines as hA(3)AR antagonists (compounds 24-27). These derivatives, though lacking the classical structural requirements for the anchoring at the hA(3) receptor site, show high hA(3) affinity and in some case selectivity versus hA(1) and hA(2A) subtypes. Molecular docking of the herein reported tricyclic and simplified derivatives was carried out to depict their hypothetical binding mode to our model of hA(3) receptor. (C) 2014 Elsevier Ltd. All rights reserved.