ethyl 6-chloro-1-(2,4-dichlorophenyl)-7-methyl-1,4-dihydroindeno[1,2-c]pyrazole-3-carboxylate | 919078-04-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: ethyl 6-chloro-1-(2,4-dichlorophenyl)-7-methyl-1,4-dihydroindeno[1,2-c]pyrazole-3-carboxylate
• 英文别名: ethyl 6-chloro-1-(2,4-dichlorophenyl)-7-methyl-4H-indeno[1,2-c]pyrazole-3-carboxylate
• CAS: 919078-04-9
• 化学式: C₂₀H₁₅Cl₃N₂O₂
• 分子量: 421.71
• InChiKey: UUFZJFHCVYJHSJ-UHFFFAOYSA-N

物化性质

• 熔点：
  245-246 °C(Solv: water (7732-18-5))
• 沸点：
  570.5±50.0 °C(Predicted)
• 密度：
  1.47±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.4
• 重原子数：
  27
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  44.1
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  ethyl 6-chloro-1-(2,4-dichlorophenyl)-7-methyl-1,4-dihydroindeno[1,2-c]pyrazole-3-carboxylate 在 氢氧化钾 作用下， 以 乙醇 、 水 为溶剂， 反应 4.0h， 以93%的产率得到6-chloro-1-(2,4-dichlorophenyl)-7-methyl-1,4-dihydroindeno[1,2-c]pyrazole-3-carboxylic acid
  参考文献：
  名称：

  Tricyclic Pyrazoles. 4. Synthesis and Biological Evaluation of Analogues of the Robust and Selective CB₂ Cannabinoid Ligand 1-(2‘,4‘-Dichlorophenyl)-6-methyl-N-piperidin-1-yl- 1,4-dihydroindeno[1,2-c]pyrazole-3-carboxamide

  摘要：

  New analogues (2a-p) of the previously reported CB2 ligands 6-methyl- and 6-chloro-1-(2',4'-dichlorophenyl)-N-piperidin-1-yl-1,4-dihydroindeno[1,2-c]pyrazole-3-carboxamides (1a,b) have been synthesized and evaluated for cannabinoid receptor affinity. One example, 1-(2',4'-dichlorophenyl)-6-methyl-N-cyclohexyilamine-1,4-dihydroindeno[1,2-c]pyrazole-3-carboxamide (2a) was shown to have single digit nanomolar affinity for cannabinoid CB2 receptors. Furthermore, compounds 2a and 2b, as well as lead structures 1a, b, were also shown to be agonist in an in vitro model based on human promyelocytic leukemia HL-60 cells.

  DOI：

  10.1021/jm060920d
• 作为产物：
  描述：

  5-氯-6-甲基-1-茚酮 在 sodium ethanolate 、 溶剂黄146 作用下， 以 乙醇 为溶剂， 反应 32.0h， 生成 ethyl 6-chloro-1-(2,4-dichlorophenyl)-7-methyl-1,4-dihydroindeno[1,2-c]pyrazole-3-carboxylate
  参考文献：
  名称：

  Tricyclic Pyrazoles. 4. Synthesis and Biological Evaluation of Analogues of the Robust and Selective CB₂ Cannabinoid Ligand 1-(2‘,4‘-Dichlorophenyl)-6-methyl-N-piperidin-1-yl- 1,4-dihydroindeno[1,2-c]pyrazole-3-carboxamide

  摘要：

  New analogues (2a-p) of the previously reported CB2 ligands 6-methyl- and 6-chloro-1-(2',4'-dichlorophenyl)-N-piperidin-1-yl-1,4-dihydroindeno[1,2-c]pyrazole-3-carboxamides (1a,b) have been synthesized and evaluated for cannabinoid receptor affinity. One example, 1-(2',4'-dichlorophenyl)-6-methyl-N-cyclohexyilamine-1,4-dihydroindeno[1,2-c]pyrazole-3-carboxamide (2a) was shown to have single digit nanomolar affinity for cannabinoid CB2 receptors. Furthermore, compounds 2a and 2b, as well as lead structures 1a, b, were also shown to be agonist in an in vitro model based on human promyelocytic leukemia HL-60 cells.

  DOI：

  10.1021/jm060920d