N-[6-(cyclohexylmethoxy)-2-(propylsulfanyl)pyrimidin-4-yl]acetamide | 1013029-54-3

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: N-[6-(cyclohexylmethoxy)-2-(propylsulfanyl)pyrimidin-4-yl]acetamide
• 英文别名: N-[6-(cyclohexylmethoxy)-2-propylsulfanylpyrimidin-4-yl]acetamide
• CAS: 1013029-54-3
• 化学式: C₁₆H₂₅N₃O₂S
• 分子量: 323.459
• InChiKey: TXTHBALAJYMVIQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  22
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  89.4
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  6-(Cyclohexylmethoxy)-2-propylsulfanylpyrimidin-4-amine 、 乙酸酐 在 硫酸 作用下， 以47%的产率得到N-[6-(cyclohexylmethoxy)-2-(propylsulfanyl)pyrimidin-4-yl]acetamide
  参考文献：
  名称：

  Derivatives of 4-Amino-6-hydroxy-2-mercaptopyrimidine as Novel, Potent, and Selective A₃ Adenosine Receptor Antagonists

  摘要：

  A number of derivatives of 4-amino-6-hydroxy-2-mercaptopyrimidine (5) were synthesized and biologically evaluated as A(3) adenosine receptor (A(3) AR) antagonists. The new compounds were designed as open chain analogues of a triazolopyrimidinone derivative displaying submicromolar affinity for the A3 AR, which had been previously identified using a 3D database search. Substituents R, R', and R" attached to the parent compound 5 were chosen according to factorial design and stepwise lead optimization approaches, taking into account the essentially hydrophobic nature of the A3 AR binding site. As a result, 5m (R = n-C3H7, R' = 4-ClC6H4CH2, R" = CH3) was identified among the pyrimidine derivatives as the ligand featuring the best combination of potency and selectivity for the target receptor. This compound binds to the A3 AR with a K-i of 3.5 nM and is devoid of appreciable affinity for the A(1), A(2A), and A(2B) ARs.

  DOI：

  10.1021/jm701159t

文献信息

• Derivatives of 4-Amino-6-hydroxy-2-mercaptopyrimidine as Novel, Potent, and Selective A₃ Adenosine Receptor Antagonists
  作者：Barbara Cosimelli、Giovanni Greco、Marina Ehlardo、Ettore Novellino、Federico Da Settimo、Sabrina Taliani、Concettina La Motta、Marusca Bellandi、Tiziano Tuccinardi、Adriano Martinelli、Osele Ciampi、Maria Letizia Trincavelli、Claudia Martini

  DOI：10.1021/jm701159t

  日期：2008.3.1

  A number of derivatives of 4-amino-6-hydroxy-2-mercaptopyrimidine (5) were synthesized and biologically evaluated as A(3) adenosine receptor (A(3) AR) antagonists. The new compounds were designed as open chain analogues of a triazolopyrimidinone derivative displaying submicromolar affinity for the A3 AR, which had been previously identified using a 3D database search. Substituents R, R', and R" attached to the parent compound 5 were chosen according to factorial design and stepwise lead optimization approaches, taking into account the essentially hydrophobic nature of the A3 AR binding site. As a result, 5m (R = n-C3H7, R' = 4-ClC6H4CH2, R" = CH3) was identified among the pyrimidine derivatives as the ligand featuring the best combination of potency and selectivity for the target receptor. This compound binds to the A3 AR with a K-i of 3.5 nM and is devoid of appreciable affinity for the A(1), A(2A), and A(2B) ARs.