3-(5-(4-氯苯基)-1-(2,4-二氯苯基)-4-甲基-1H-吡唑-3-基)-5-异丙基-1,2,4-恶二唑 | 1016556-18-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 中文名称: 3-(5-(4-氯苯基)-1-(2,4-二氯苯基)-4-甲基-1H-吡唑-3-基)-5-异丙基-1,2,4-恶二唑
• 英文名称: 3-(5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4-methyl-1H-pyrazol-3-yl)-5-isopropyl-1,2,4-oxadiazole
• 英文别名: 3-[5-(4-Chlorophenyl)-1-(2,4-dichlorophenyl)-4-methylpyrazol-3-yl]-5-propan-2-yl-1,2,4-oxadiazole
• CAS: 1016556-18-5
• 化学式: C₂₁H₁₇Cl₃N₄O
• 分子量: 447.751
• InChiKey: KVZGKCSKXLWWOX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.9
• 重原子数：
  29
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  56.7
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  (Z)-5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-N'-hydroxy-4-methyl-1H-pyrazole-3-carboximidamide 、 异丁酰氯 以 甲苯 为溶剂， 反应 2.0h， 以74%的产率得到3-(5-(4-氯苯基)-1-(2,4-二氯苯基)-4-甲基-1H-吡唑-3-基)-5-异丙基-1,2,4-恶二唑
  参考文献：
  名称：

  Bioisosteric replacement of the pyrazole 3-carboxamide moiety of rimonabant. A novel series of oxadiazoles as CB1 cannabinoid receptor antagonists

  摘要：

  基于利莫那班的吡唑C3-酰胺的生物等排替换为五元氧二氮杂环，发现了一类新型氧二氮杂环衍生物，具有有希望的生物活性，对CB1受体具有活性。其中，含有强吸电子基团（例如，CF3）和立体有利的大体积基团（例如，叔丁基）的烷基链路的化合物表现出优异的CB1拮抗作用和选择性，因此可能作为进一步开发为抗肥胖药物的潜在候选。

  DOI：

  10.1039/b807648k

文献信息

• Heteroaryl-Pyrazole Derivatives as Cannabinoid CB1 Receptor Antagonists
  申请人：LEE Jinhwa

  公开号：US20080081812A1

  公开（公告）日：2008-04-03

  A heteroaryl-pyrazole compound of formula (I) or a pharmaceutically acceptable salt thereof is effective as a cannabinoid CB 1 receptor inverse agonist or antagonist, which is useful for preventing or treating obesity and obesity-related metabolic disorders. The present invention also provides a method for preparing the inventive heteroaryl-pyrasole compounds or a pharmaceutically acceptable salt thereof, a pharmaceutical composition containing same, and a method for preventing or treating obesity and obesity-related metabolic disorders.

  一种异芳基-吡唑化合物，其公式为(I)或其药用可接受盐，可作为大麻素CB1受体的反向激动剂或拮抗剂，用于预防或治疗肥胖及其相关代谢紊乱。本发明还提供了制备本发明的异芳基-吡唑化合物或其药用可接受盐的方法，包含该化合物的药物组合物，以及用于预防或治疗肥胖及其相关代谢紊乱的方法。
• Heteroaryl-pyrazole derivatives as cannabinoid CB1 receptor antagonists
  申请人：Lee Jinhwa

  公开号：US20080081815A1

  公开（公告）日：2008-04-03

  A novel heteroaryl-pyrazole compound of formula (I) or a pharmaceutically acceptable salt thereof is effective as a cannabinoid CB 1 receptor inverse agonist or antagonist, which is useful for preventing or treating obesity and obesity-related metabolic disorders. The prevention also provide a method for preparing same, a pharmaceutical composition containing same, and a method for preventing or treating obesity and obesity-related metabolic disorders.

  化合物I式的新型杂环基吡唑化合物或其药学上可接受的盐，作为大麻素CB1受体的反向激动剂或拮抗剂，对于预防或治疗肥胖症和肥胖相关代谢紊乱是有效的。该预防还提供了一种制备方法、包含该化合物的制药组合物以及预防或治疗肥胖症和肥胖相关代谢紊乱的方法。
• US7875647B2
  申请人：——

  公开号：US7875647B2

  公开（公告）日：2011-01-25
• Bioisosteric replacement of the pyrazole 3-carboxamide moiety of rimonabant. A novel series of oxadiazoles as CB1 cannabinoid receptor antagonists
  作者：Cheng-Ming Chu、Ming-Shiu Hung、Min-Tsang Hsieh、Chun-Wei Kuo、Suja T. D.、Jen-Shin Song、Hua-Hao Chiu、Yu-Sheng Chao、Kak-Shan Shia

  DOI：10.1039/b807648k

  日期：——

  Based on the bioisosteric replacement of the pyrazole C3-carboxamide of rimonabant with a 5-alkyl oxadiazole ring, a novel class of oxadiazole derivatives with promising biological activity towards CB1 receptors was discovered. Among them, compounds with an alkyl linker containing a strong electron-withdrawing group (e.g., CF3) and a sterically favorable bulky group (e.g., t-butyl) exhibited excellent CB1 antagonism and selectivity, and thus might serve as potential candidates for further development as anti-obesity agents.

  基于利莫那班的吡唑C3-酰胺的生物等排替换为五元氧二氮杂环，发现了一类新型氧二氮杂环衍生物，具有有希望的生物活性，对CB1受体具有活性。其中，含有强吸电子基团（例如，CF3）和立体有利的大体积基团（例如，叔丁基）的烷基链路的化合物表现出优异的CB1拮抗作用和选择性，因此可能作为进一步开发为抗肥胖药物的潜在候选。