6-Anilino-3-methylsulfanyl-1-(4-nitrophenyl)-5-phenylpyrazolo[3,4-d]pyrimidin-4-one | 1413477-14-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 6-Anilino-3-methylsulfanyl-1-(4-nitrophenyl)-5-phenylpyrazolo[3,4-d]pyrimidin-4-one
• 英文别名: 6-anilino-3-methylsulfanyl-1-(4-nitrophenyl)-5-phenylpyrazolo[3,4-d]pyrimidin-4-one
• CAS: 1413477-14-1
• 化学式: C₂₄H₁₈N₆O₃S
• 分子量: 470.511
• InChiKey: YVOPUBDCCLRCPO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  34
• 可旋转键数：
  5
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.04
• 拓扑面积：
  134
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  6-Anilino-3-methylsulfanyl-1-(4-nitrophenyl)-5-phenylpyrazolo[3,4-d]pyrimidin-4-one 、 4-硝基苯胺 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以64%的产率得到6-Anilino-3-(4-nitroanilino)-1-(4-nitrophenyl)-5-phenylpyrazolo[3,4-d]pyrimidin-4-one
  参考文献：
  名称：

  Novel 3-substituted-1-aryl-5-phenyl-6-anilinopyrazolo[3,4-d]pyrimidin-4-ones: Docking, synthesis and pharmacological evaluation as a potential anti-inflammatory agents

  摘要：

  Novel 3-substituted-1-aryl-5-phenyl-6-anilino-pyrazolo[3,4-d]pyrimidin-4-ones of pharmacological significance were synthesized by the reaction of ethyl-(5-amino-3-methylthio-1-aryl-5-phenyl-2H-pyrazole)-4-carboxylates 3a-c with S-methyl diphenyl thiourea independently to produce 1-aryl-3-thiomethyl-5-phenyl-pyrazolo[3,4-d]pyrimidines 4a-c in DMF with catalytic amount of K2CO3, which on further treatment with different aromatic amines independently under same reaction conditions generated for compounds 5a-l. The compounds were screened for the anti-inflammatory activity and evaluated for ulcerogenic potential. The compounds 5i exhibited superior anti-inflammatory activity in comparison with diclofenac sodium and comparable activity with celecoxib at a dose of 25 mg/kg. The other compounds 4c, 5c, 5f and 5l were found as active with inhibition of edema in the range of 35-39 after 3 h of administration of test compounds. The ulcerogenic potential of active compounds was observed to be quite lesser as compared to standard. COX-2 docking score of the active compound 5i was found to be better than standard celecoxib. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.08.119
• 作为产物：
  描述：

  4-硝基苯肼 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 6-Anilino-3-methylsulfanyl-1-(4-nitrophenyl)-5-phenylpyrazolo[3,4-d]pyrimidin-4-one
  参考文献：
  名称：

  Novel 3-substituted-1-aryl-5-phenyl-6-anilinopyrazolo[3,4-d]pyrimidin-4-ones: Docking, synthesis and pharmacological evaluation as a potential anti-inflammatory agents

  摘要：

  Novel 3-substituted-1-aryl-5-phenyl-6-anilino-pyrazolo[3,4-d]pyrimidin-4-ones of pharmacological significance were synthesized by the reaction of ethyl-(5-amino-3-methylthio-1-aryl-5-phenyl-2H-pyrazole)-4-carboxylates 3a-c with S-methyl diphenyl thiourea independently to produce 1-aryl-3-thiomethyl-5-phenyl-pyrazolo[3,4-d]pyrimidines 4a-c in DMF with catalytic amount of K2CO3, which on further treatment with different aromatic amines independently under same reaction conditions generated for compounds 5a-l. The compounds were screened for the anti-inflammatory activity and evaluated for ulcerogenic potential. The compounds 5i exhibited superior anti-inflammatory activity in comparison with diclofenac sodium and comparable activity with celecoxib at a dose of 25 mg/kg. The other compounds 4c, 5c, 5f and 5l were found as active with inhibition of edema in the range of 35-39 after 3 h of administration of test compounds. The ulcerogenic potential of active compounds was observed to be quite lesser as compared to standard. COX-2 docking score of the active compound 5i was found to be better than standard celecoxib. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.08.119