5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-N'-(2,2-dimethylpropanoyl)-4-methyl-1H-pyrazole-3-carbohydrazide

• 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)-N'-(2,2-dimethylpropanoyl)-4-methyl-1H-pyrazole-3-carbohydrazide
• 英文别名: 5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-N'-(2,2-dimethylpropanoyl)-4-methylpyrazole-3-carbohydrazide
• 化学式: C₂₂H₂₁Cl₃N₄O₂
• 分子量: 479.793
• InChiKey: KZOLRNZKXITSTG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.3
• 重原子数：
  31
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  76
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-N'-(2,2-dimethylpropanoyl)-4-methyl-1H-pyrazole-3-carbohydrazide 在 对甲苯磺酸 、 碳酸氢钠 作用下， 以 水 、 甲苯 为溶剂， 反应 18.0h， 生成 2-tert-butyl-5-(5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4-methyl-1H-pyrazol-3-yl)-1,3,4-oxadiazole
  参考文献：
  名称：

  (1,5-DIPHENYL-1H-PYRAZOL-3-YL)OXADIAZOLE DERIVATIVES, PREPARATION METHOD THEREOF AND USE OF SAME IN THERAPEUTICS

  摘要：

  该发明涉及具有以下化学式（I）的化合物：其中R1、R2、R3和R4如本文所定义。该发明还涉及制备所述化合物的方法以及在治疗中的应用。

  公开号：

  US20080039510A1
• 作为产物：
  描述：

  5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4-methyl-1H-pyrazole-3-carbohydrazide 、 三甲基乙酸 在 N-甲基吗啉 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以87%的产率得到5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-N'-(2,2-dimethylpropanoyl)-4-methyl-1H-pyrazole-3-carbohydrazide
  参考文献：
  名称：

  Pentacycle derivatives 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 pentacycle derivatives. Five of the new compounds which displayed high in vitro rCB1 binding affinities were assayed for binding to hCB2 receptor. Noticeably, 2-(5-(4-bromophenyl)-1-(2,4-dichlorophenyl)-4-(5-methyl- 1,3,4-thiadiazol-2-yl)-1H-pyrazol-3-yl)-5-(1-(trifluoromethyl) cyclopropyl)-1,3,4-oxadiazole (16l) demonstrated good binding affinity and decent selectivity for rCB1 receptor (IC50 = 1.72 nM, hCB2/rCB1 = 142). (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.10.015

文献信息

• Biarylpyrazolyl Oxadiazole as Potent, Selective, Orally Bioavailable Cannabinoid-1 Receptor Antagonists for the Treatment of Obesity
  作者：Suk Ho Lee、Hee Jeong Seo、Sung-Han Lee、Myung Eun Jung、Ji-Hyun Park、Hyun-Ju Park、Jakyung Yoo、Hoseop Yun、Jooran Na、Suk Youn Kang、Kwang-Seop Song、Min-ah Kim、Chong-Hwan Chang、Jeongmin Kim、Jinhwa Lee

  DOI：10.1021/jm800843r

  日期：2008.11.27

  Since the CB1 cannabinoid receptor antagonist 1 (SR141716, rimonabant) was previously reported to modulate food intake, CB1 antagonism has been considered as a new therapeutic target for the treatment of obesity. In the present study, biarylpyrazole analogues based on a pyrazole core coupled with 1,3,4-oxadiazole were synthesized and tested for CB1 receptor binding affinity. Thorough SAR studies to optimize pyrazole substituents as well as 1,3,4-oxadiazole ring led to several novel CB1 antagonists with IC50 similar to 1 nM for the CB1 receptor binding. Among these analogues, we identified 2-(4-((1H-1,2,4-triazol-1-yl)methyl)-5-(4-bromophenyl)-1-(2,4-dichlorophenyl)-1H-pyrazol-3-yl)-5-(1-(trifluoromethyl)cyclopropyl)-1,3,4-oxa- diazole 43c as a promising precandidate for the development as an antiobesity agent.
• Fluid dispersion, and thermosensitive recording material and method for preparing the same
  申请人：Ricoh Company, Ltd.

  公开号：EP1834800B1

  公开（公告）日：2009-10-14
• US7632852B2
  申请人：——

  公开号：US7632852B2

  公开（公告）日：2009-12-15