6-acetamiddo-4-methoxy-2-methylthiopyrimidine | 98594-55-9

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 6-acetamiddo-4-methoxy-2-methylthiopyrimidine
• 英文别名: N-(6-methoxy-2-methylsulfanyl-pyrimidin-4-yl)-acetamide；N-(6-Methoxy-2-methylmercapto-pyrimidin-4-yl)-acetamid；N-[6-methoxy-2-(methylsulfanyl)pyrimidin-4-yl]acetamide；N-(6-methoxy-2-methylsulfanylpyrimidin-4-yl)acetamide
• CAS: 98594-55-9
• 化学式: C₈H₁₁N₃O₂S
• 分子量: 213.26
• InChiKey: QEGWPRMLVDYOAP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  89.4
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  6-acetamiddo-4-methoxy-2-methylthiopyrimidine 在 水 、 镍 作用下， 生成 N-(6-methoxy-pyrimidin-4-yl)-acetamide
  参考文献：
  名称：

  Pfleiderer; Liedek, Justus Liebigs Annalen der Chemie, 1958, vol. 612, p. 163,164

  摘要：

  DOI：
• 作为产物：
  描述：

  6-氨基-4-甲氧基-2-甲基硫脲嘧啶 、 乙酸酐 在 硫酸 作用下， 以60%的产率得到6-acetamiddo-4-methoxy-2-methylthiopyrimidine
  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

• 6-Acetamido-4-methoxy-2-methylthiopyrimidine
  作者：J. N. Low、G. Ferguson、J. Cobo、M. Melguizo、M. Nogueras、A. Sanchez

  DOI：10.1107/s0108270196003423

  日期：1996.8.15

  Molecules of the title compound, 4-methoxy-2-methyl-thio-6-pyrimidinylacetamide, C8H11N3O2S, lie on crystallographic mirror planes and are linked by N-H ... O hydrogen bonds to form zigzag ribbons running parallel to the a axis, with an N ... O distance of 3.018 (2) Angstrom.