5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-3-(1-hydroxy-2,2,2-trifluoroethyl)-4-methyl-1H-pyrazole | 1430408-27-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-3-(1-hydroxy-2,2,2-trifluoroethyl)-4-methyl-1H-pyrazole
• 英文别名: 1-[5-(4-Chlorophenyl)-1-(2,4-dichlorophenyl)-4-methylpyrazol-3-yl]-2,2,2-trifluoroethanol；1-[5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4-methylpyrazol-3-yl]-2,2,2-trifluoroethanol
• CAS: 1430408-27-7
• 化学式: C₁₈H₁₂Cl₃F₃N₂O
• 分子量: 435.66
• InChiKey: QUPFCTPNQLZVHO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.1
• 重原子数：
  27
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  38
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-3-(1-hydroxy-2,2,2-trifluoroethyl)-4-methyl-1H-pyrazole 在 草酰氯 、 二甲基亚砜 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 0.25h， 以99%的产率得到5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4-methyl-3-(1-oxo-2,2,2-trifluoroethyl)-1H-pyrazole
  参考文献：
  名称：

  Novel pyrazole derivatives as neutral CB 1 antagonists with significant activity towards food intake

  摘要：

  In spite of rimonabant's withdrawal from the European market due to its adverse effects, interest in the development of drugs based on CB1 antagonists is revamping on the basis of the peculiar properties of this class of compounds. In particular, new strategies have been proposed for the treatment of obesity and/or related risk factors through CB1, antagonists, i.e. by the development of selectively peripherally acting agents or by the identification of neutral CB1 antagonists. New compounds based on the lead 031 antagonist/inverse agonist rimonabant have been synthesized with focus on obtaining neutral CB1 antagonists. Amongst the new derivatives described in this paper, the mixture of the two enantiomers (+/-)-5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-3-(2-cyclohexyl-1-hydroxyethyl)-4-methyl-1H-pyrazole ((+/-)-5), and compound 5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-3-[(4-2-cyclohexyl-1-fluorovinyl]-4-methyl-1H-pyrazole ((Z)-6), showed interesting pharmacological profiles. According to the preliminary pharmacological evaluation, these novel pyrazole derivatives showed in fact both neutral CB1 antagonism behaviour and significant in vivo activity towards food intake. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2012.12.056
• 作为产物：
  描述：

  5-(4-氯苯基)-1-(2,4-二氯苯基)-4-甲基-1H-吡唑-3-羧酸乙酯 在 lithium aluminium tetrahydride 、 四丁基氟化铵 、 三甲基铝 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 为溶剂， 反应 17.75h， 生成 5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-3-(1-hydroxy-2,2,2-trifluoroethyl)-4-methyl-1H-pyrazole
  参考文献：
  名称：

  Novel pyrazole derivatives as neutral CB 1 antagonists with significant activity towards food intake

  摘要：

  In spite of rimonabant's withdrawal from the European market due to its adverse effects, interest in the development of drugs based on CB1 antagonists is revamping on the basis of the peculiar properties of this class of compounds. In particular, new strategies have been proposed for the treatment of obesity and/or related risk factors through CB1, antagonists, i.e. by the development of selectively peripherally acting agents or by the identification of neutral CB1 antagonists. New compounds based on the lead 031 antagonist/inverse agonist rimonabant have been synthesized with focus on obtaining neutral CB1 antagonists. Amongst the new derivatives described in this paper, the mixture of the two enantiomers (+/-)-5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-3-(2-cyclohexyl-1-hydroxyethyl)-4-methyl-1H-pyrazole ((+/-)-5), and compound 5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-3-[(4-2-cyclohexyl-1-fluorovinyl]-4-methyl-1H-pyrazole ((Z)-6), showed interesting pharmacological profiles. According to the preliminary pharmacological evaluation, these novel pyrazole derivatives showed in fact both neutral CB1 antagonism behaviour and significant in vivo activity towards food intake. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2012.12.056