4-chloro-N-[4-imino-2-(2-phenylethyl)pyrazolo[3,4-d]pyrimidin-5-yl]benzamide | 1221500-08-8

• 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: 4-chloro-N-[4-imino-2-(2-phenylethyl)pyrazolo[3,4-d]pyrimidin-5-yl]benzamide
• CAS: 1221500-08-8
• 化学式: C₂₀H₁₇ClN₆O
• 分子量: 392.848
• InChiKey: XSLIHXVSCPNIMA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  28
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  86.4
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  2-碘代乙基苯 、 4-氯苯甲酰肼 、 原甲酸三乙酯 、 3-氨基-4-氰基吡唑 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 、 甲乙醚 为溶剂， 生成 4-chloro-N-[4-imino-2-(2-phenylethyl)pyrazolo[3,4-d]pyrimidin-5-yl]benzamide 、 4-Chloro-N-(4-imino-1-phenethyl-1,4-dihydro-pyrazolo[3,4-d]pyrimidin-5-yl)-benzamide
  参考文献：
  名称：

  Does the combination of optimal substitutions at the C2-, N5- and N8-positions of the pyrazolo-triazolo-pyrimidine scaffold guarantee selective modulation of the human A3 adenosine receptors?

  摘要：

  In an attempt to study the optimal combination of a phenyl ring at the C-2-position and different substituents at the N-5- and N-8-positions towards the selective modulation of human A(3) adenosine receptors (hA(3)AR), we synthesized a new series of 2-para-(un)substituted-phenyl-pyrazolo-triazolo-pyrimidines bearing either a methyl or phenylethyl at N-8 and chains of variable length at N-5. Through biological evaluation, it was found that the majority of the compounds had good affinities towards the hA(3)AR in the low nanomolar range. Compound 16 possessed the best hA(3)AR affinity and selectivity profile (K(i)hA(3) = 1.33 nM; hA(1)/hA(3) = 4880; hA(2A)/hA(3) = 1100) in the present series of2-(substituted)phenylpyrazolo-triazolo-pyrimidine derivatives. In addition to pharmacological characterization, a molecular modeling investigation on these compounds further elucidated the effect of different substituents at the pyrazolo-triazolo-pyrimidine scaffold on affinity and selectivity to hA3AR. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.08.026