ethyl 7-chloro-1-(2',4'-dichlorophenyl)-4,5-dihydro-1H-benzo[g]indazole-3-carboxylate | 337526-52-0

• 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 7-chloro-1-(2',4'-dichlorophenyl)-4,5-dihydro-1H-benzo[g]indazole-3-carboxylate
• 英文别名: ethyl ester of 7-chloro-1-(2,4-dichlorophenyl)-4,5-dihydro-1H-benzo[g]indazole-3-carboxylic acid；ethyl 7-chloro-1-(2,4-dichlorophenyl)-4,5-dihydrobenzo[g]indazole-3-carboxylate
• CAS: 337526-52-0
• 化学式: C₂₀H₁₅Cl₃N₂O₂
• 分子量: 421.71
• InChiKey: SAWAXBPVVDFEMX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.3
• 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 7-chloro-1-(2',4'-dichlorophenyl)-4,5-dihydro-1H-benzo[g]indazole-3-carboxylate 在 氢氧化钾 、 氯化亚砜 作用下， 以 甲醇 、 甲苯 为溶剂， 生成
  参考文献：
  名称：

  Tricyclic pyrazoles. Part 2: Synthesis and biological evaluation of novel 4,5-dihydro-1H-benzo[g]indazole-based ligands for cannabinoid receptors

  摘要：

  A series of 4,5-dihydro-1H-benzo[g]indazole-3-carboxamides (2a-k) as analogues of the previously reported CB2 ligands 6-chloro- and 6-methyl-1-(2',4'-dichlorophenyl)-N-piperidin-1-yl-1,4-dihydroindeno[1,2-c]pyrazole-3-carboxamides (1a,b) was synthesized and their affinity and selectivity towards CB1 and CB2 receptors were evaluated. Several of the new compounds (2a,b,c,d and i) exhibited CB1 affinity in the nanomolar range with moderate or negligible affinity towards CB2 receptors. Compounds 2a and c increased intestinal propulsion in mouse. Their pro-kinetic effects were reversed by the reference CB agonist CP-55,940. Consequently, in vivo CB1 antagonistic activity was highlighted for these compounds. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.02.032
• 作为产物：
  描述：

  6-氯-3,4-二氢-2H-1-萘酮 在 sodium ethanolate 作用下， 以 乙醇 为溶剂， 反应 5.5h， 生成 ethyl 7-chloro-1-(2',4'-dichlorophenyl)-4,5-dihydro-1H-benzo[g]indazole-3-carboxylate
  参考文献：
  名称：

  Tricyclic pyrazoles. Part 2: Synthesis and biological evaluation of novel 4,5-dihydro-1H-benzo[g]indazole-based ligands for cannabinoid receptors

  摘要：

  A series of 4,5-dihydro-1H-benzo[g]indazole-3-carboxamides (2a-k) as analogues of the previously reported CB2 ligands 6-chloro- and 6-methyl-1-(2',4'-dichlorophenyl)-N-piperidin-1-yl-1,4-dihydroindeno[1,2-c]pyrazole-3-carboxamides (1a,b) was synthesized and their affinity and selectivity towards CB1 and CB2 receptors were evaluated. Several of the new compounds (2a,b,c,d and i) exhibited CB1 affinity in the nanomolar range with moderate or negligible affinity towards CB2 receptors. Compounds 2a and c increased intestinal propulsion in mouse. Their pro-kinetic effects were reversed by the reference CB agonist CP-55,940. Consequently, in vivo CB1 antagonistic activity was highlighted for these compounds. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.02.032

文献信息

• Pyrazolecarboxylic acid tricyclic derivatives, preparation and pharmaceutical compositions containing same
  申请人：Barth Francis

  公开号：US06906080B1

  公开（公告）日：2005-06-14

  The subject of the invention is tricyclic derivatives of pyrazolecarboxylic acid of formula: in which R 1 represents a C 3 -C 15 carboxyl radical or an NR 2 R 3 group. The invention also relates to the method for preparing the compounds of formula (I), pharmaceutical compositions containing them. The compounds of formula (I) are active on cannabinoid CB 1 receptors.

  本发明涉及式中的吡唑羧酸三环衍生物：其中R1代表C3-C15羧基基团或NR2R3基团。本发明还涉及制备式(I)化合物的方法，含有这些化合物的药物组合物。式(I)化合物对大麻素CB1受体具有活性。