Ethyl 5-(4-bromophenyl)-1-(2,4-dichlorophenyl)-4-(hydroxymethyl)pyrazole-3-carboxylate | 501423-60-5

• 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 5-(4-bromophenyl)-1-(2,4-dichlorophenyl)-4-(hydroxymethyl)pyrazole-3-carboxylate
• CAS: 501423-60-5
• 化学式: C₁₉H₁₅BrCl₂N₂O₃
• 分子量: 470.15
• InChiKey: QCIROOINGHEJCD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  27
• 可旋转键数：
  6
• 环数：
  3.0
• 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：

  三异丙基氯硅烷 、 Ethyl 5-(4-bromophenyl)-1-(2,4-dichlorophenyl)-4-(hydroxymethyl)pyrazole-3-carboxylate 在 咪唑 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成
  参考文献：
  名称：

  Oxadiazole-diarylpyrazole 4-carboxamides as cannabinoid CB1 receptor ligands

  摘要：

  Cannabinoid CB-1 receptors have been the focus of extensive studies since the first clinical results of rimonabant (SR141716) for the treatment of obesity and obesity-related metabolic disorders were reported in 2001. To further evaluate the properties of CB receptors, we have designed and efficiently prepared a series of oxadiazole-diarylpyrazole 4-carboxamides. Six of the new compounds which displayed high in vitro CB1 binding affinities were assayed for binding to CB2 receptor. Noticeably, 5-(4-bromophenyl)-3-(5-tert-butyl-1,3,4-oxadiazol-2-yl)-1-(2,4-dichlorophenyl)-N-phenyl-1H-pyrazole-4-carboxamide (12q) and 5-(4-bromophenyl)-3-(5-tert-butyl-1,3,4-oxadiazol-2-yl)-1-(2,4-dichlorophenyl)-N-(pyridin-2-yl)-1H-pyrazole-4-carboxamide (12r) demonstrated good binding affinity and decent selectivity for CB1 receptor (IC50 = 1.35 nM, CB2/CB1 = 286 for 12q; IC50 = 1.46 nM, CB2/CB1 = 256 for 12r). (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.02.063
• 作为产物：
  描述：

  ethyl 4-(bromomethyl)-5-(4-bromophenyl)-1-(2,4-dichlorophenyl)-1H-pyrazole-3-carboxylate 在 silver nitrate 作用下， 以 水 、 丙酮 为溶剂， 生成 Ethyl 5-(4-bromophenyl)-1-(2,4-dichlorophenyl)-4-(hydroxymethyl)pyrazole-3-carboxylate
  参考文献：
  名称：

  Oxadiazole-diarylpyrazole 4-carboxamides as cannabinoid CB1 receptor ligands

  摘要：

  Cannabinoid CB-1 receptors have been the focus of extensive studies since the first clinical results of rimonabant (SR141716) for the treatment of obesity and obesity-related metabolic disorders were reported in 2001. To further evaluate the properties of CB receptors, we have designed and efficiently prepared a series of oxadiazole-diarylpyrazole 4-carboxamides. Six of the new compounds which displayed high in vitro CB1 binding affinities were assayed for binding to CB2 receptor. Noticeably, 5-(4-bromophenyl)-3-(5-tert-butyl-1,3,4-oxadiazol-2-yl)-1-(2,4-dichlorophenyl)-N-phenyl-1H-pyrazole-4-carboxamide (12q) and 5-(4-bromophenyl)-3-(5-tert-butyl-1,3,4-oxadiazol-2-yl)-1-(2,4-dichlorophenyl)-N-(pyridin-2-yl)-1H-pyrazole-4-carboxamide (12r) demonstrated good binding affinity and decent selectivity for CB1 receptor (IC50 = 1.35 nM, CB2/CB1 = 286 for 12q; IC50 = 1.46 nM, CB2/CB1 = 256 for 12r). (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.02.063

文献信息

• US7393842B2
  申请人：——

  公开号：US7393842B2

  公开（公告）日：2008-07-01
• US7745440B2
  申请人：——

  公开号：US7745440B2

  公开（公告）日：2010-06-29
• US8084467B2
  申请人：——

  公开号：US8084467B2

  公开（公告）日：2011-12-27