2-(tert-butyl)-5-(5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4-(((triisopropylsilyl)oxy)methyl)-1H-pyrazol-3-yl)-1,3,4-oxadiazole | 1150311-16-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 2-(tert-butyl)-5-(5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4-(((triisopropylsilyl)oxy)methyl)-1H-pyrazol-3-yl)-1,3,4-oxadiazole
• CAS: 1150311-16-2
• 化学式: C₃₁H₃₉Cl₃N₄O₂Si
• 分子量: 634.121
• InChiKey: WLVUFLKEVXLTHR-UHFFFAOYSA-N

物化性质

• 沸点：
  679.9±65.0 °C(predicted)
• 密度：
  1.22±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  10.54
• 重原子数：
  41.0
• 可旋转键数：
  9.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  65.97
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  2-(tert-butyl)-5-(5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4-(((triisopropylsilyl)oxy)methyl)-1H-pyrazol-3-yl)-1,3,4-oxadiazole 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 生成 (3-(5-叔丁基-1,3,4-恶二唑-2-基)-5-(4-氯苯基)-1-(2,4-二氯苯基)-1H-吡唑-4-基)甲醇
  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：

  在 伯吉斯试剂 作用下， 以 四氢呋喃 为溶剂， 生成 2-(tert-butyl)-5-(5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4-(((triisopropylsilyl)oxy)methyl)-1H-pyrazol-3-yl)-1,3,4-oxadiazole
  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