N-[2-(4-bromophenyl)-8-methylpyrazolo[4,3-e][1,2,4]triazolo-[1,5-c]pyrimidin-5-yl]phenylacetamide | 1221499-92-8

• 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-[2-(4-bromophenyl)-8-methylpyrazolo[4,3-e][1,2,4]triazolo-[1,5-c]pyrimidin-5-yl]phenylacetamide
• 英文别名: N-[4-(4-bromophenyl)-11-methyl-3,5,6,8,10,11-hexazatricyclo[7.3.0.02,6]dodeca-1(12),2,4,7,9-pentaen-7-yl]-2-phenylacetamide
• CAS: 1221499-92-8
• 化学式: C₂₁H₁₆BrN₇O
• 分子量: 462.308
• InChiKey: VRVDXRJXVUQQEP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  30
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  90
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  2-(4-bromophenyl)-8-methylpyrazolo[4,3-e]-1,2,4-triazolo[1,5-c]-pyrimidin-5-amine 、 苯乙酰氯 在 N,N-二异丙基乙胺 作用下， 以 甲苯 为溶剂， 以63%的产率得到N-[2-(4-bromophenyl)-8-methylpyrazolo[4,3-e][1,2,4]triazolo-[1,5-c]pyrimidin-5-yl]phenylacetamide
  参考文献：
  名称：

  The Significance of 2-Furyl Ring Substitution with a 2-(para-substituted) Aryl Group in a New Series of Pyrazolo-triazolo-pyrimidines as Potent and Highly Selective hA₃ Adenosine Receptors Antagonists: New Insights into Structure−Affinity Relationship and Receptor−Antagonist Recognition

  摘要：

  Among the heterocyclic structures identified as potent human A(3) (hA(3)) adenosine receptor's antagonists, we have demonstrated that the new pyrazolo-triazolo-pyrimidines, bearing an aryl group in replacement of the C-2-furyl ring, not only confer a good pharmacological profile (with significantly enhanced selectivity against other adenosine receptor subytpes) but also overcome the metabolic transformation of the furan ring into toxic intermediates. All the synthesized [2-(para-substituted) phenyl]-pyrazolo-triazolo-pyrimidines showed affinity at the hA(3) receptor in the low nanomolar range. The most potent derivative of the series presented better affinity and excellent selectivity (compound 31, K-i hA(3) = 0.108 nM; hA(1)/hA(3) = 5200; hA(2A)/hA(3) = 7200), in comparison to the C-2-furyl counterpart. A receptor-driven molecular modeling investigation, based on a recently proposed model of A(3) receptor derived from the crystallographic structure of human A(2A) receptor, has been carried out in order to support the experimental binding data and to justify the enhanced selectivity against the other receptor subtypes.

  DOI：

  10.1021/jm100049f