1-Methyl-6-(2-oxo-2-phenyl-ethylsulfanyl)-1,5-dihydro-pyrazolo[3,4-d]pyrimidin-4-one | 152423-05-7

• 英文名称: 1-Methyl-6-(2-oxo-2-phenyl-ethylsulfanyl)-1,5-dihydro-pyrazolo[3,4-d]pyrimidin-4-one
• 英文别名: 1-methyl-6-phenacylsulfanyl-5H-pyrazolo[3,4-d]pyrimidin-4-one
• CAS: 152423-05-7
• 化学式: C₁₄H₁₂N₄O₂S
• 分子量: 300.341
• InChiKey: PKLRQENOYJHFMH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  102
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1-Methyl-6-(2-oxo-2-phenyl-ethylsulfanyl)-1,5-dihydro-pyrazolo[3,4-d]pyrimidin-4-one 在 盐酸 作用下， 以 1,4-二氧六环 、 乙醇 为溶剂， 反应 10.0h， 生成 1-甲基-1H-吡唑并[3,4-d]嘧啶-4,6(5H,7H)-二酮
  参考文献：
  名称：

  Pyrazolothiazolopyrimidine derivatives as a novel class of anti-inflammatory or antinociceptive agents: synthesis, structural characterization and pharmacological evaluation

  摘要：

  As a part of a research program on anti-inflammatory-analgesic compounds, pyrazolothiazolopyrimidines 5a-f and 5g-i were prepared by cyclodehydration in 98% H2SO4 or PPA of the corresponding 6-thioketomethylene-substituted-4-hydroxy-pyrazolo[3,4-d]pyrimidines 2a-i and 2g-i. The results of the pharmacological in vivo screening indicate an interesting dissociation of the analgesic from the anti-inflammatory activity depending on aromatic or aliphatic substitution at the C4 of the thiazole ring. Analgesic activity was not associated with any narcotic effect; in addition, all the active compounds showed a remarkable systemic and gastric tolerance. This indicated a mode of action different from that of the classical nonsteroidal anti-inflammatory drugs, acting on prostaglandin biosynthesis. To clarify the mechanism or the mechanisms underlying the pharmacological activity of these and other closely related compounds, we initiated a 'file chemical approach' to various systems involved in the inflammatory process. At present, some of the more active in vivo compounds tested as substance P antagonists showed a moderate and possibly non-specific effect on NK1 and NK2 receptors.

  DOI：

  10.1016/0223-5234(93)90123-v
• 作为产物：
  描述：

  2-溴苯乙酮 、 1-methyl-6-sulfanyl-5H-pyrazolo[3,4-d]pyrimidin-4-one 在 sodium carbonate 作用下， 以 丙酮 为溶剂， 反应 24.0h， 以25%的产率得到1-Methyl-6-(2-oxo-2-phenyl-ethylsulfanyl)-1,5-dihydro-pyrazolo[3,4-d]pyrimidin-4-one
  参考文献：
  名称：

  Pyrazolothiazolopyrimidine derivatives as a novel class of anti-inflammatory or antinociceptive agents: synthesis, structural characterization and pharmacological evaluation

  摘要：

  As a part of a research program on anti-inflammatory-analgesic compounds, pyrazolothiazolopyrimidines 5a-f and 5g-i were prepared by cyclodehydration in 98% H2SO4 or PPA of the corresponding 6-thioketomethylene-substituted-4-hydroxy-pyrazolo[3,4-d]pyrimidines 2a-i and 2g-i. The results of the pharmacological in vivo screening indicate an interesting dissociation of the analgesic from the anti-inflammatory activity depending on aromatic or aliphatic substitution at the C4 of the thiazole ring. Analgesic activity was not associated with any narcotic effect; in addition, all the active compounds showed a remarkable systemic and gastric tolerance. This indicated a mode of action different from that of the classical nonsteroidal anti-inflammatory drugs, acting on prostaglandin biosynthesis. To clarify the mechanism or the mechanisms underlying the pharmacological activity of these and other closely related compounds, we initiated a 'file chemical approach' to various systems involved in the inflammatory process. At present, some of the more active in vivo compounds tested as substance P antagonists showed a moderate and possibly non-specific effect on NK1 and NK2 receptors.

  DOI：

  10.1016/0223-5234(93)90123-v