6-[2-(4-Bromo-phenyl)-2-oxo-ethylsulfanyl]-1,5-dihydro-pyrazolo[3,4-d]pyrimidin-4-one | 152423-01-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 6-[2-(4-Bromo-phenyl)-2-oxo-ethylsulfanyl]-1,5-dihydro-pyrazolo[3,4-d]pyrimidin-4-one
• 英文别名: 6-[2-(4-Bromophenyl)-2-oxoethyl]sulfanyl-1,5-dihydropyrazolo[3,4-d]pyrimidin-4-one；6-[2-(4-bromophenyl)-2-oxoethyl]sulfanyl-1,5-dihydropyrazolo[3,4-d]pyrimidin-4-one
• CAS: 152423-01-3
• 化学式: C₁₃H₉BrN₄O₂S
• 分子量: 365.21
• InChiKey: XMWMMVHIRNDNEW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  108
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  6-[2-(4-Bromo-phenyl)-2-oxo-ethylsulfanyl]-1,5-dihydro-pyrazolo[3,4-d]pyrimidin-4-one 在 硫酸 作用下， 反应 120.0h， 以98%的产率得到6-(4-Bromo-phenyl)-1H-pyrazolo[3,4-d]thiazolo[3,2-a]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
• 作为产物：
  描述：

  4-羟基-6-巯基吡唑(3,4-D)嘧啶 、 2,4'-二溴苯乙酮 在 sodium carbonate 作用下， 以 丙酮 为溶剂， 反应 24.0h， 以80%的产率得到6-[2-(4-Bromo-phenyl)-2-oxo-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

文献信息

• Pyrazolothiazolopyrimidine derivatives as a novel class of anti-inflammatory or antinociceptive agents: synthesis, structural characterization and pharmacological evaluation
  作者：F Russo、S Guccione、G Romeo、G Uccello Barretta、S Pucci、A Caruso、M Amico-Roxas、V Cutuli

  DOI：10.1016/0223-5234(93)90123-v

  日期：1993.1

  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.