6-chloro-1-(2,4-dichlorophenyl)-7-methyl-1,4-dihydroindeno[1,2-c]pyrazole-3-carboxylic acid | 919077-98-8

• 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-chloro-1-(2,4-dichlorophenyl)-7-methyl-1,4-dihydroindeno[1,2-c]pyrazole-3-carboxylic acid
• 英文别名: 6-chloro-1-(2,4-dichlorophenyl)-7-methyl-4H-indeno[1,2-c]pyrazole-3-carboxylic acid
• CAS: 919077-98-8
• 化学式: C₁₈H₁₁Cl₃N₂O₂
• 分子量: 393.657
• InChiKey: QYMJUSDCGHPOCQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  25
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  55.1
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  6-chloro-1-(2,4-dichlorophenyl)-7-methyl-1,4-dihydroindeno[1,2-c]pyrazole-3-carboxylic acid 、 1-氨基哌啶 在 1-羟基苯并三唑 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 20.0h， 以54%的产率得到6-chloro-1-(2’,4’-dichlorophenyl)-7-methyl-N-piperidin-1-yl-1,4-dihydroindeno[1,2-c]pyrazole-3-carboxamide
  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：

  2,4-二氯苯肼盐酸盐 在 氢氧化钾 、 溶剂黄146 作用下， 以 乙醇 、 水 为溶剂， 反应 12.0h， 生成 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