1-(2,4-二氯苯基)-4-甲基-5-(4-甲氧基苯基)-1H-吡唑-3-羧酸乙酯 | 501426-48-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 中文名称: 1-(2,4-二氯苯基)-4-甲基-5-(4-甲氧基苯基)-1H-吡唑-3-羧酸乙酯
• 英文名称: 1-(2,4-dichlorophenyl)-4-methyl-5-(4-methoxyphenyl)-1H-pyrazole-3-carboxylic acid ethyl ester
• 英文别名: 1-(2,4-dichlorophenyl)-5-(4-methoxyphenyl)-4-methyl-1H-pyrazole-3-carboxylic acid ethyl ester；1-(2,4-dichloro-phenyl)-5-(4-methoxy-phenyl)-4-methyl-1H-pyrazole-3-carboxylic acid ethyl ester；5-(4-methoxyphenyl)-1-(2,4-dichlorophenyl)-4-methyl-1H-pyrazole-3-carboxylic acid ethyl ester；ethyl 1-(2,4-dichlorophenyl)-5-(4-methoxyphenyl)-4-methylpyrazole-3-carboxylate
• CAS: 501426-48-8
• 化学式: C₂₀H₁₈Cl₂N₂O₃
• 分子量: 405.281
• InChiKey: SGBQJOOVICPVOO-UHFFFAOYSA-N

物化性质

• 熔点：
  96-97 °C
• 沸点：
  529.6±50.0 °C(Predicted)
• 密度：
  1.30±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  27
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  53.4
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-(2,4-二氯苯基)-4-甲基-5-(4-甲氧基苯基)-1H-吡唑-3-羧酸乙酯 在 氢氧化钾 、 氢溴酸 作用下， 以 甲醇 、 溶剂黄146 为溶剂， 反应 16.0h， 生成 1-(2,4-二氯苯基)-5-(4-羟基苯基)-4-甲基-1H-吡唑-3-羧酸
  参考文献：
  名称：

  Synthesis, Structure−Activity Relationship, and Evaluation of SR141716 Analogues:  Development of Central Cannabinoid Receptor Ligands with Lower Lipophilicity

  摘要：

  Exploration of the central CB1 cannabinoid receptors using positron emission tomography (PET) will allow for an understanding of the pharmacological and physiological role played by these receptors in the CNS. Current tracers are highly lipophilic compounds that exhibit very high nonspecific to specific binding ratios and as a result are inapt for use in humans. We have synthesized a series of less lipophilic analogues of SR141716 to serve as potential radioligands. Binding affinities of the series and a functional electrophysiological assay of three of our compounds have been presented.

  DOI：

  10.1021/jm020157x
• 作为产物：
  描述：

  ethyl 2-[(2,4-dichlorophenyl)hydrazinylidene]-4-(4-methoxyphenyl)-3-methyl-4-oxobutanoate 在 溶剂黄146 作用下， 反应 24.0h， 以1.63 g的产率得到1-(2,4-二氯苯基)-4-甲基-5-(4-甲氧基苯基)-1H-吡唑-3-羧酸乙酯
  参考文献：
  名称：

  Discovery of 2-[5-(4-Chloro-phenyl)-1-(2,4-dichloro-phenyl)-4-ethyl-1H-pyrazol-3-yl]-1,5,5-trimethyl-1,5-dihydro-imidazol-4-thione (BPR-890) via an Active Metabolite. A Novel, Potent and Selective Cannabinoid-1 Receptor Inverse Agonist with High Antiobesity Efficacy in DIO Mice

  摘要：

  By using the active metabolite 5 as an initial template, further structural modifications led to the identification of the titled compound 24 (BPR-890) as a highly potent CB I inverse agonist possessing an excellent CB2/1 selectivity and remarkable in vivo efficacy in diet-induced obese mice with a minimum effective dose as low as 0.03 mg/kg (po qd) at the end of the 30-day chronic study. Current SAR studies along with those of many existing rimonabant-mimicking molecules imply that around the pyrazole C3-position, a rigid and deep binding pocket should exist for CB1 receptor. In addition, relative to the conventional carboxamide carbonyl, serving as a key hydrogen-bond acceptor during ligand-CB1 receptor interaction, the corresponding polarizable thione carbonyl might play a more critical role in stabilizing the Asp366-Lys192 salt bridge in the proposed CB1-receptor homology model and inducing significant selectivity for CB1R over CB2R.

  DOI：

  10.1021/jm900471u

文献信息

• Imidazol-4-one and Imidazole-4-thione Compounds
  申请人：Shia Kak-Shan

  公开号：US20100113546A1

  公开（公告）日：2010-05-06

  Imidazol-4-one or imidazole-4-thione compounds of formula (I): wherein X, R 1 , R 2 , R 3 , R 4 , R 5 , and R 6 are defined herein. Also disclosed is a method for treating a cannabinoid receptor-mediated disorder with these compounds.

  咪唑-4-酮或咪唑-4-硫酮化合物的化学式（I）：其中X，R1，R2，R3，R4，R5和R6在此定义。还揭示了使用这些化合物治疗大麻素受体介导的疾病的方法。
• Therapeutic Agents
  申请人：Cheng Leifeng

  公开号：US20080146614A1

  公开（公告）日：2008-06-19

  The present invention relates to 1,5-diphenylpyrazole compounds of formula I (A chemical formula should be inserted here—please see paper copy enclosed herewith) and processes for preparing such compounds, their use in the treatment of obesity, psychiatric and neurological disorders, to methods for their therapeutic use and to pharmaceutical compositions containing them.

  本发明涉及式I的1,5-二苯基吡唑化合物（化学式应在此处插入-请参见随附的纸质副本）以及制备这些化合物的过程，它们在肥胖症、精神和神经疾病的治疗中的应用，以及它们的治疗应用方法和含有它们的制药组合物。
• “One-Pot” Synthesis of 4-Substituted 1,5-Diaryl-1H-pyrazole-3-carboxylic Acids via a MeONa/LiCl-Mediated Sterically Hindered Claisen Condensation–Knorr Reaction–Hydrolysis Sequence
  作者：Ya-Fei Ji、Jian-An Jiang、Cai-Yan Du、Chun-Hui Gu

  DOI：10.1055/s-0032-1317668

  日期：——

  A "one-pot" synthesis of 4-substituted 1,5-diaryl-1H-pyrazole-3-carboxylic acids was first reported in moderate to good yields. This concise procedure, featuring efficiency and green chemistry, was composed of MeONa/LiCl-mediated sterically hindered Claisen condensation, Knorr reaction and hydrolysis.
• WO2007/148061
  申请人：——

  公开号：——

  公开（公告）日：——
• WO2007/148062
  申请人：——

  公开号：——

  公开（公告）日：——