3-[1-[4-(methylsulfonyl) phenyl]-4-(trifluoromethyl)-1H-imidazol-2-yl]pyridine | 177660-77-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 3-[1-[4-(methylsulfonyl) phenyl]-4-(trifluoromethyl)-1H-imidazol-2-yl]pyridine
• 英文别名: 1-(4-methylsulfonylphenyl)-2-(pyridin-3-yl)-4-trifluoromethyl-imidazole；3-[1-(4-methanesulfonylphenyl)-4-trifluoromethyl-1H-imidazol-2-yl]-pyridine；3-[1-[4-(methylsulfonyl)phenyl]-4-trifluoromethyl-1H-imidazol-2-yl]pyridine；3-[1-(4-methylsulfonylphenyl)-4-(trifluoromethyl)imidazol-2-yl]pyridine
• CAS: 177660-77-4
• 化学式: C₁₆H₁₂F₃N₃O₂S
• 分子量: 367.351
• InChiKey: ZJOUYQCSZYKGKU-UHFFFAOYSA-N

物化性质

• 熔点：
  193 °C
• 沸点：
  564.8±60.0 °C(Predicted)
• 密度：
  1.42±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  25
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  73.2
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  3-[1-[4-(methylsulfonyl) phenyl]-4-(trifluoromethyl)-1H-imidazol-2-yl]pyridine 在 四丁基氟化铵 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 3.0h， 生成 4-[2-(pyridin-3-yl)-4-(trifluoromethyl)-1H-imidazol-1-yl]benzenesulfonamide
  参考文献：
  名称：

  Selective Cyclooxygenase-2 Inhibitors:  Heteroaryl Modified 1,2-Diarylimidazoles Are Potent, Orally Active Antiinflammatory Agents

  摘要：

  A series of heteroaryl modified 1,2-diarylimidazoles has been synthesized and found to be potent and highly selective (1000-9000-fold) inhibitors of the human COX-2. 3-Pyridyl derived COX-2 selective inhibitor (25) exhibited excellent activity in acute (carrageenan induced paw edema, ED50 = 5.4 mg/kg) and chronic (adjuvant induced arthritis, ED50 = 0.25 mg/kg) models of inflammation. The relatively long half-life of 25 in rat and dog prompted investigation of the pyridyl and other heteroaromatic systems containing potential metabolic functionalities. A number of substituted pyridyl and thiazole containing compounds (e.g., 44, 46, 54, 76, and 78) demonstrated excellent oral activity in every efficacy model evaluated. Several orally active diarylimidazoles exhibited desirable pharmacokinetics profiles and showed no CI toxicity in the rat up to 100 mg/kg in both acute and chronic models. The paper describes facile and practical syntheses of the targeted diarylimidazoles. The structure-activity relationships and antiinflammatory properties of a series of diarylimidazoles are discussed.

  DOI：

  10.1021/jm0000719
• 作为产物：
  描述：

  3-氰基吡啶 在 Oxone 、 sodium hexamethyldisilazane 、 碳酸氢钠 、 对甲苯磺酸 作用下， 以 四氢呋喃 、 甲醇 、 水 、 异丙醇 为溶剂， 反应 16.5h， 生成 3-[1-[4-(methylsulfonyl) phenyl]-4-(trifluoromethyl)-1H-imidazol-2-yl]pyridine
  参考文献：
  名称：

  Selective Cyclooxygenase-2 Inhibitors:  Heteroaryl Modified 1,2-Diarylimidazoles Are Potent, Orally Active Antiinflammatory Agents

  摘要：

  A series of heteroaryl modified 1,2-diarylimidazoles has been synthesized and found to be potent and highly selective (1000-9000-fold) inhibitors of the human COX-2. 3-Pyridyl derived COX-2 selective inhibitor (25) exhibited excellent activity in acute (carrageenan induced paw edema, ED50 = 5.4 mg/kg) and chronic (adjuvant induced arthritis, ED50 = 0.25 mg/kg) models of inflammation. The relatively long half-life of 25 in rat and dog prompted investigation of the pyridyl and other heteroaromatic systems containing potential metabolic functionalities. A number of substituted pyridyl and thiazole containing compounds (e.g., 44, 46, 54, 76, and 78) demonstrated excellent oral activity in every efficacy model evaluated. Several orally active diarylimidazoles exhibited desirable pharmacokinetics profiles and showed no CI toxicity in the rat up to 100 mg/kg in both acute and chronic models. The paper describes facile and practical syntheses of the targeted diarylimidazoles. The structure-activity relationships and antiinflammatory properties of a series of diarylimidazoles are discussed.

  DOI：

  10.1021/jm0000719

文献信息

• 1,2-aryl and heteroaryl substituted imidazolyl compounds for the
  申请人：GD Searle & Co

  公开号：US05616601A1

  公开（公告）日：1997-04-01

  A class of imidazolyl compounds is described for use in treating inflammation and inflammation-related disorders. Compounds of particular interest are defined by Formula I: ##STR1## wherein R.sup.1 -R.sup.6 are as described in the specification; or a pharmaceutically-acceptable salt thereof.

  描述了一类咪唑基化合物，用于治疗炎症和与炎症相关的疾病。特别感兴趣的化合物由以下式I定义：##STR1##其中R.sup.1 -R.sup.6如规范中所述；或其药用盐。
• Combination therapy for the treatment of cancer
  申请人：Pharmacia Corporation

  公开号：US20030216410A1

  公开（公告）日：2003-11-20

  The present invention relates to methods for treatment or prevention of neoplasia disorders using protein tyrosine kinase inhibitors in combination with cyclooxygenase inhibitors, in particular cyclooxygenase-2 selective inhibitors.

  本发明涉及使用蛋白酪氨酸激酶抑制剂与环氧合酶抑制剂，特别是环氧合酶-2选择性抑制剂，联合治疗或预防肿瘤性疾病的方法。
• Antiangiogenic combination therapy for the treatment of cancer
  申请人：——

  公开号：US20020103141A1

  公开（公告）日：2002-08-01

  The present invention provides combinations of a DNA topoisomerase I inhibiting agent and a selective COX-2 inhibiting agent for preventing, treating, and/or reducing the risk of developing a neoplasia disorder in a mammal.

  本发明提供了一种DNA拓扑异构酶I抑制剂和选择性COX-2抑制剂的组合物，用于预防、治疗和/或减少哺乳动物发生肿瘤性疾病的风险。
• Compositions of a cyclooxygenase-2 selective inhibitor and a sodium ion channel blocker for the treatment of pain, inflammation or inflammation mediated disorders
  申请人：Pharmacia Corporation

  公开号：US20040220187A1

  公开（公告）日：2004-11-04

  The present invention provides compositions and methods for the treatment of pain, inflammation or inflammation-mediated disorders in a subject. More particularly, the invention provides a combination therapy for the treatment of pain, inflammation or inflammation mediated disorders comprising the administration to a subject of a sodium ion channel blocker in combination with a cyclooxygenase-2 selective inhibitor.

  本发明提供了用于治疗疼痛、炎症或炎症介导性疾病的组合物和方法。更具体地，本发明提供了一种联合疗法，用于治疗疼痛、炎症或炎症介导性疾病，包括向受试者施用钠离子通道阻滞剂与环氧合酶-2选择性抑制剂的组合。
• [EN] CANNABINOID ACID ESTER COMPOSITIONS AND USES THEREOF<br/>[FR] COMPOSITIONS D'ESTER D'ACIDE CANNABINOÏDE ET LEURS UTILISATIONS
  申请人：EPM GROUP INC

  公开号：WO2020186010A1

  公开（公告）日：2020-09-17

  The present disclosure provides pharmaceutical compositions including a cannabinoid acid ester compound alone or in combination with one or more additional cannabinoid compounds. In some embodiments, the cannabinoid acid ester compound is a cannabidiolic acid ester. A variety of therapeutic applications in which the cannabinoid acid ester compounds and pharmaceutical compositions find use are also provided, including combination therapies using cannabinoid acid ester compounds and one or more additional therapeutic agents.

  本公开提供了包括大麻酸酯化合物在内或与一个或多个额外的大麻化合物结合的药物组合物。在一些实施例中，大麻酸酯化合物是大麻二酚酸酯。还提供了大麻酸酯化合物和药物组合物在多种治疗应用中的使用，包括使用大麻酸酯化合物和一个或多个额外治疗剂的联合疗法。