N-(piperidin-1-yl)-1-(2,4-dichlorophenyl)-5-{4-(5-hydroxypentyl)phenyl}-4-methyl-1H-pyrazole-3-carboxamide | 850554-42-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: N-(piperidin-1-yl)-1-(2,4-dichlorophenyl)-5-{4-(5-hydroxypentyl)phenyl}-4-methyl-1H-pyrazole-3-carboxamide
• 英文别名: 1-(2,4-dichlorophenyl)-5-[4-(5-hydroxypentyl)phenyl]-4-methyl-N-piperidin-1-ylpyrazole-3-carboxamide
• CAS: 850554-42-6
• 化学式: C₂₇H₃₂Cl₂N₄O₂
• 分子量: 515.483
• InChiKey: DIPLQGOOMULNJW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.7
• 重原子数：
  35
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  70.4
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-(piperidin-1-yl)-1-(2,4-dichlorophenyl)-5-{4-(5-hydroxypentyl)phenyl}-4-methyl-1H-pyrazole-3-carboxamide 以 N,N-二甲基甲酰胺 为溶剂， 反应 48.0h， 生成 5-[4-(5-cyanopentyl)phenyl]-1-(2,4-dichlorophenyl)-4-methyl-N-piperidin-1-ylpyrazole-3-carboxamide
  参考文献：
  名称：

  Synthesis of novel 5-substituted pyrazole derivatives as cannabinoid antagonists

  摘要：

  A facile seven-step sequence was developed from 4'-bromopropiophenone, utilizing a Suzuki-type coupling with an alkene, to give several novel 5-substituted pyrazole derivatives in overall yields of 11-31%. They are potent CB1 antagonists and have binding affinities similar to SR 141716A. Like SR 141716A, they may prove to be clinically useful for the treatment of obesity. (C) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2005.01.165
• 作为产物：
  描述：

  2-(pent-4-en-1-yloxy)tetrahydro-2H-pyran 在 9-borabicyclo[3.3.1]nonane dimer 、 三甲基铝 、 对甲苯磺酸 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 125.0h， 生成 N-(piperidin-1-yl)-1-(2,4-dichlorophenyl)-5-{4-(5-hydroxypentyl)phenyl}-4-methyl-1H-pyrazole-3-carboxamide
  参考文献：
  名称：

  Synthesis of novel 5-substituted pyrazole derivatives as cannabinoid antagonists

  摘要：

  A facile seven-step sequence was developed from 4'-bromopropiophenone, utilizing a Suzuki-type coupling with an alkene, to give several novel 5-substituted pyrazole derivatives in overall yields of 11-31%. They are potent CB1 antagonists and have binding affinities similar to SR 141716A. Like SR 141716A, they may prove to be clinically useful for the treatment of obesity. (C) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2005.01.165

文献信息

• Methoxy- and Fluorine-Substituted Analogs of O-1302: Synthesis and in Vitro Binding Affinity for the CB1 Cannabinoid Receptor
  作者：Shintaro Tobiishi、Toru Sasada、Yumiko Nojiri、Fumihiko Yamamoto、Takahiro Mukai、Kiichi Ishiwata、Minoru Maeda

  DOI：10.1248/cpb.55.1213

  日期：——

  respective amine with pyrazole carboxylic acid, in order to develop tracers for medical imaging. Their potency for inhibiting the binding of the CB1 antagonist [(3)H]SR141716 was evaluated with the aim of developing positron emission tomography (PET) ligands for the cerebral cannabinoid CB1 receptor. These analogs bearing a piperidinyl carboxamide at the C(3) of the pyrazole ring exhibited affinities

  在N-（哌啶基）-1-（2,4-二氯苯基）-4-甲基-5-（4-戊基苯基）-1H-吡唑-3-甲酰胺的戊基链的末端碳上取代的甲氧基和氟类似物（ O-1302）是由N-（哌啶基）-5-（4-氯苯基）-1-的1,5-二芳基吡唑核心模板基于5-苯基-1-戊醇合成而成的多步方法（2,4-二氯苯基）-4-甲基-1H-吡唑-3-羧酰胺（SR141716）通过将相应的胺与吡唑羧酸缩合，以开发用于医学成像的示踪剂。为了开发脑大麻素CB1受体的正电子发射断层扫描（PET）配体，评估了它们抑制CB1拮抗剂[（3）H] SR141716结合的能力。这些类似物在吡唑环的C（3）处带有哌啶子基羧酰胺，其亲和力与CB1参考拮抗剂SR141716相当，因此需要使用放射性标记的形式进行进一步的生物学成像研究。在吡唑环的C（3）处取代的吗啉环导致CB1亲和力降低。
• Heteropyrazole analogs acting on cannabinoid receptors
  申请人：University of Connecticut

  公开号：EP2368881A1

  公开（公告）日：2011-09-28

  Pyrazole analogues of formula wherein R1, R2, R3, R4, A and B are as defined in the specification, are disclosed. Such compounds are antagonists for the CB1 and/or CB2 cannabinoid receptors. Also disclosed are pharmaceutical preparations containing such compounds, and the compounds for use in treating various disorders.

  式中的吡唑类似物 其中 R1、R2、R3、R4、A 和 B 如说明书中所定义。这类化合物是 CB1 和/或 CB2 大麻受体的拮抗剂。还公开了含有此类化合物的药物制剂，以及用于治疗各种疾病的化合物。