7-chloro-1-(4'-methoxyphenyl)-4,5-dihydro-1H-benzo[g]indazole-3-carboxylic acid | 56457-19-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 7-chloro-1-(4'-methoxyphenyl)-4,5-dihydro-1H-benzo[g]indazole-3-carboxylic acid
• 英文别名: 7-Chloro-1-(4-methoxyphenyl)-4,5-dihydrobenzo[g]indazole-3-carboxylic acid
• CAS: 56457-19-3
• 化学式: C₁₉H₁₅ClN₂O₃
• 分子量: 354.793
• InChiKey: CAVVGSSIOQUZMC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  25
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  64.4
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  7-chloro-1-(4'-methoxyphenyl)-4,5-dihydro-1H-benzo[g]indazole-3-carboxylic acid 在 氯化亚砜 作用下， 以 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：

  4-甲氧基苯肼盐酸盐 在 氢氧化钾 作用下， 以 甲醇 、 乙醇 为溶剂， 反应 3.0h， 生成 7-chloro-1-(4'-methoxyphenyl)-4,5-dihydro-1H-benzo[g]indazole-3-carboxylic acid
  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

• US3940418A
  申请人：——

  公开号：US3940418A

  公开（公告）日：1976-02-24
• Tricyclic pyrazoles. Part 2: Synthesis and biological evaluation of novel 4,5-dihydro-1H-benzo[g]indazole-based ligands for cannabinoid receptors
  作者：Gabriele Murineddu、Stefania Ruiu、Jean-Mario Mussinu、Giovanni Loriga、Giuseppe E. Grella、Mauro A.M. Carai、Paolo Lazzari、Luca Pani、Gérard A. Pinna

  DOI：10.1016/j.bmc.2005.02.032

  日期：2005.5

  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.