N-[2-(cyclohexylthio)-4-oxo-6-phenylthieno[2,3-d]pyrimidin-3(4H)-yl]methanesulfonamide | 1415720-15-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻吩并嘧啶酮衍生物
• 英文名称: N-[2-(cyclohexylthio)-4-oxo-6-phenylthieno[2,3-d]pyrimidin-3(4H)-yl]methanesulfonamide
• 英文别名: N-(2-cyclohexylsulfanyl-4-oxo-6-phenylthieno[2,3-d]pyrimidin-3-yl)methanesulfonamide
• CAS: 1415720-15-8
• 化学式: C₁₉H₂₁N₃O₃S₃
• 分子量: 435.592
• InChiKey: VRNNETZNAHYOJJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  28
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  141
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  碘环己烷 、 N-(4-oxo-6-phenyl-2-thioxo-1,4-dihydrothieno[2,3-d]pyrimidin-3(2H)-yl)methanesulfonamide 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 以45%的产率得到N-[2-(cyclohexylthio)-4-oxo-6-phenylthieno[2,3-d]pyrimidin-3(4H)-yl]methanesulfonamide
  参考文献：
  名称：

  Sulfonilamidothiopyrimidone and thiopyrimidone derivatives as selective COX-2 inhibitors: Synthesis, biological evaluation, and docking studies

  摘要：

  Newly synthesized sulfonilamidothiopyrimidone derivatives and a subset of 14 sulfonilamidothiopyrimidones and thiopyrimidones selected by an MTT assays cell viability guided selection from an in house collection were evaluated to determine the inhibitory effect on the PGE(2) formation in human peripheral blood lymphocytes (PBLs) using commercial ELISA. The newly synthesized sulfonilamidothiopyrimidone derivatives showed interesting pharmacological activities. Preliminary in vitro assays showed that compounds 2-5 are endowed with very high activity. Compound 2 was the most active as hCOX-2 inhibitor. The observed effects were not due to an inhibition of cell proliferation as proved by the BrdU assay. Western blot of COX-2 confirmed the inhibition on the PGE(2) secretion. Further evidence on the inhibitory potential and selectivity as COX-2 inhibitors of the selected compounds came from the in vitro screening. In order to better rationalize the action and the binding mode of these compounds, docking studies were carried out. These studies were in agreement with the biological data. Compounds 2-5 were able to fit into the active site of COX-2 with highest scores and interaction energies. Furthermore, compound 2, which showed an inhibition of around 50% on PGE(2) production, was the best scored in all the docking calculations carried out. (C) 2012 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2012.09.005