7-甲基-2-苯基-咪唑并[1,2-a][1,3,5]三嗪-4-胺 | 478813-62-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 三嗪类
• 中文名称: 7-甲基-2-苯基-咪唑并[1,2-a][1,3,5]三嗪-4-胺
• 英文名称: 7-Methyl-2-phenyl-imidazo[1,2-a][1,3,5]triazin-4-ylamine
• 英文别名: 7-methyl-2-phenylimidazo[1,2-a][1,3,5]triazin-4-amine
• CAS: 478813-62-6
• 化学式: C₁₂H₁₁N₅
• 分子量: 225.253
• InChiKey: OFMKYUJLYPYZDV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  69.1
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  溴代环戊烷 、 7-甲基-2-苯基-咪唑并[1,2-a][1,3,5]三嗪-4-胺 在 potassium carbonate 、 potassium iodide 作用下， 以 乙腈 为溶剂， 以41%的产率得到Cyclopentyl-(7-methyl-2-phenyl-imidazo[1,2-a][1,3,5]triazin-4-yl)-amine
  参考文献：
  名称：

  Design, Synthesis and Biological Evaluation of Novel N-Alkyl- and N-Acyl-(7-substituted-2-phenylimidazo[1,2-a][1,3,5]triazin-4-yl)amines (ITAs) as Novel A₁ Adenosine Receptor Antagonists

  摘要：

  Prompted by pharmacophore and docking based models, we have synthesized and tested a number of N-alkyl and N-acyl-(7-substituted-2-phenylimidazo[1,2-alpha] [1,3,5]triazin-4-yl)amines (ITAs, 7) designed as a new class of A(1) adenosine receptor (A(1)AR) antagonists. Binding affinities at the A(1)AR, A(2A)AR, and A(3)AR were determined using bovine cerebral membranes. Most of the compounds displayed K-i values at the A(1)AR in the submicromolar or even in the low nanomolar range, thus confirming the rationale leading to their synthesis. All or most of the ligands turned out to be selective for the A(1)AR over the A(2A)AR and A(3)AR subtypes, respectively. Structure-affinity relationships at the A(1)AR were rationalized by docking simulations in terms of putative ligand/receptor interactions. Among the ITAs investigated, 1-[(7-methyl-2-phenyl-imidazo[1,2-alpha][1,3,5]triazin-4-yl)amino] acetone (7j) exhibited the best combination of affinity at the A(1)AR (K-i = 12 nM) and selectivity over the A(2A)AR and A(3)AR subtypes (K(i)s > 10000 nM).

  DOI：

  10.1021/jm020911e
• 作为产物：
  描述：

  2,4-二氨基-6-苯基-1,3,5-三嗪 、 一氯丙酮 在 molecular sieve 作用下， 以 乙醇 为溶剂， 以43%的产率得到7-甲基-2-苯基-咪唑并[1,2-a][1,3,5]三嗪-4-胺
  参考文献：
  名称：

  Design, Synthesis and Biological Evaluation of Novel N-Alkyl- and N-Acyl-(7-substituted-2-phenylimidazo[1,2-a][1,3,5]triazin-4-yl)amines (ITAs) as Novel A₁ Adenosine Receptor Antagonists

  摘要：

  Prompted by pharmacophore and docking based models, we have synthesized and tested a number of N-alkyl and N-acyl-(7-substituted-2-phenylimidazo[1,2-alpha] [1,3,5]triazin-4-yl)amines (ITAs, 7) designed as a new class of A(1) adenosine receptor (A(1)AR) antagonists. Binding affinities at the A(1)AR, A(2A)AR, and A(3)AR were determined using bovine cerebral membranes. Most of the compounds displayed K-i values at the A(1)AR in the submicromolar or even in the low nanomolar range, thus confirming the rationale leading to their synthesis. All or most of the ligands turned out to be selective for the A(1)AR over the A(2A)AR and A(3)AR subtypes, respectively. Structure-affinity relationships at the A(1)AR were rationalized by docking simulations in terms of putative ligand/receptor interactions. Among the ITAs investigated, 1-[(7-methyl-2-phenyl-imidazo[1,2-alpha][1,3,5]triazin-4-yl)amino] acetone (7j) exhibited the best combination of affinity at the A(1)AR (K-i = 12 nM) and selectivity over the A(2A)AR and A(3)AR subtypes (K(i)s > 10000 nM).

  DOI：

  10.1021/jm020911e

文献信息

• Design, Synthesis and Biological Evaluation of Novel <i>N</i>-Alkyl- and <i>N</i>-Acyl-(7-substituted-2-phenylimidazo[1,2-<i>a</i>][1,3,5]triazin-4-yl)amines (ITAs) as Novel A₁ Adenosine Receptor Antagonists
  作者：Ettore Novellino、Enrico Abignente、Barbara Cosimelli、Giovanni Greco、Manuela Iadanza、Sonia Laneri、Antonio Lavecchia、Maria Grazia Rimoli、Federico Da Settimo、Giampaolo Primofiore、Daniela Tuscano、Letizia Trincavelli、Claudia Martini

  DOI：10.1021/jm020911e

  日期：2002.11.1

  Prompted by pharmacophore and docking based models, we have synthesized and tested a number of N-alkyl and N-acyl-(7-substituted-2-phenylimidazo[1,2-alpha] [1,3,5]triazin-4-yl)amines (ITAs, 7) designed as a new class of A(1) adenosine receptor (A(1)AR) antagonists. Binding affinities at the A(1)AR, A(2A)AR, and A(3)AR were determined using bovine cerebral membranes. Most of the compounds displayed K-i values at the A(1)AR in the submicromolar or even in the low nanomolar range, thus confirming the rationale leading to their synthesis. All or most of the ligands turned out to be selective for the A(1)AR over the A(2A)AR and A(3)AR subtypes, respectively. Structure-affinity relationships at the A(1)AR were rationalized by docking simulations in terms of putative ligand/receptor interactions. Among the ITAs investigated, 1-[(7-methyl-2-phenyl-imidazo[1,2-alpha][1,3,5]triazin-4-yl)amino] acetone (7j) exhibited the best combination of affinity at the A(1)AR (K-i = 12 nM) and selectivity over the A(2A)AR and A(3)AR subtypes (K(i)s > 10000 nM).