4-[6-amino-5-(cyano-NNO-azoxy)-4-cyclohexylmethoxypyrimidin-2-ylamino]-amino-N-(2-hydroxyethyl)-benzenesulfonamide | 1470134-36-1

• 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-[6-amino-5-(cyano-NNO-azoxy)-4-cyclohexylmethoxypyrimidin-2-ylamino]-amino-N-(2-hydroxyethyl)-benzenesulfonamide
• 英文别名: [4-Amino-6-(cyclohexylmethoxy)-2-[4-(2-hydroxyethylsulfamoyl)anilino]pyrimidin-5-yl]-cyanoimino-oxidoazanium
• CAS: 1470134-36-1
• 化学式: C₂₀H₂₆N₈O₅S
• 分子量: 490.543
• InChiKey: LWXURRMEKPTBNZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  34
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  213
• 氢给体数：
  4
• 氢受体数：
  12

反应信息

• 作为产物：
  描述：

  4-[[4-amino-6-(cyclohexylmethoxy)-5-nitrosopyrimidin-2-yl]amino]-N-(2-hydroxyethyl)benzenesulfonamide 、 氰胺 在 碘苯二乙酸 作用下， 以 乙腈 为溶剂， 反应 2.0h， 以86%的产率得到4-[6-amino-5-(cyano-NNO-azoxy)-4-cyclohexylmethoxypyrimidin-2-ylamino]-amino-N-(2-hydroxyethyl)-benzenesulfonamide
  参考文献：
  名称：

  6-Cyclohexylmethoxy-5-(cyano-NNO-azoxy)pyrimidine-4-amine: A new scaffold endowed with potent CDK2 inhibitory activity

  摘要：

  Substitution of the cyano-NNO-azoxy moiety (NC-N=(O)N-) for the nitroso group in NU6027, a potent and selective CDK2 inhibitor, affords a compound with slightly improved potency and comparable selectivity profile. A molecular modelling study indicates for this new scaffold a binding mode similar to the one adopted by other purine and pyrimidine analogues, and suggests a relevant role for a conserved water molecule in stabilizing the bioactive pose of this and other pyrimidine ligands. The introduction of aminosulfonylphenyl substituents on the 2-amino group of the pyrimidine increased the CDK2 inhibitory potency by two orders of magnitude, while maintaining the same degree of selectivity. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.07.031