5-Methanesulfonyl-2-(5-phenyl-3-trifluoromethyl-pyrazol-1-yl)-pyridine | 343628-59-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 5-Methanesulfonyl-2-(5-phenyl-3-trifluoromethyl-pyrazol-1-yl)-pyridine
• 英文别名: 5-methylsulfonyl-2-[5-phenyl-3-(trifluoromethyl)pyrazol-1-yl]pyridine
• CAS: 343628-59-1
• 化学式: C₁₆H₁₂F₃N₃O₂S
• 分子量: 367.351
• InChiKey: SCVTWTWDHRDTKP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 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：

  5-Methanesulfonyl-2-(5-phenyl-3-trifluoromethyl-pyrazol-1-yl)-pyridine 在 N-氯代丁二酰亚胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 2-(4-Chloro-5-phenyl-3-trifluoromethyl-pyrazol-1-yl)-5-methanesulfonyl-pyridine
  参考文献：
  名称：

  Discovery of a potent, selective and orally active canine COX-2 inhibitor, 2-(3-difluoromethyl-5-phenyl-pyrazol-1-yl)-5-methanesulfonyl-pyridine

  摘要：

  Structure-activity relationship (SAR) studies of 2-[3-di(and tri)fluoromethyl-5-arylpyrazol-1-yl]-5-methanesulfonylpyridine derivatives for canine COX enzymes are described. This led to the identification of 12a as a lead candidate for further progression. The in vitro and in vivo activity of 12a for the canine COX-2 enzyme as well as its in vivo efficacy and pharmacokinetic properties in dog are highlighted. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2003.10.004
• 作为产物：
  描述：

  苯乙酮 在 硫酸 、 sodium methylate 作用下， 以 乙二醇二甲醚 、 乙醇 为溶剂， 生成 5-Methanesulfonyl-2-(5-phenyl-3-trifluoromethyl-pyrazol-1-yl)-pyridine
  参考文献：
  名称：

  Discovery of a potent, selective and orally active canine COX-2 inhibitor, 2-(3-difluoromethyl-5-phenyl-pyrazol-1-yl)-5-methanesulfonyl-pyridine

  摘要：

  Structure-activity relationship (SAR) studies of 2-[3-di(and tri)fluoromethyl-5-arylpyrazol-1-yl]-5-methanesulfonylpyridine derivatives for canine COX enzymes are described. This led to the identification of 12a as a lead candidate for further progression. The in vitro and in vivo activity of 12a for the canine COX-2 enzyme as well as its in vivo efficacy and pharmacokinetic properties in dog are highlighted. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2003.10.004

文献信息

• New hydroxy-pyrazoline intermediates, subtle regio-selectivity and relative reaction rate variations observed during acid catalyzed and neutral pyrazole cyclization
  作者：Timothy Norris、Roberto Colon-Cruz、David H. B. Ripin

  DOI：10.1039/b500413f

  日期：——

  capability of the R and Ar substituents. The reaction conditions that caused cyclization to pyrazoles varied from direct condensation of the hydrazine and 1,3-dicarbonyl compounds, to reactions requiring catalytic quantities of sulfuric acid to sulfuric acid in excess. Unexpected regio-selectivity was observed in the case of R = CF3 that depended upon the reaction conditions.

  芳肼4和1,3-二羰基化合物5通过via异构体对6和7失水而反应生成吡唑，这会产生两种可能的区域异构体。有时观察到3-羟基-3,4-二氢吡唑或羟基吡唑啉9和9是稳定的可分离中间体，可以在失去第二分子水生成吡唑10和11之前对其进行充分表征。类型8和9的中间体相对较少。我们研究了其中R = CH3，CHF2和CF3，Ar = Ph和5-甲磺酰基吡啶-2--2-基的反应系列（方案2），并观察了动力学行为和区域异构现象之间的性质差异，具体取决于电子的程度。 R和Ar取代基的吸收能力。导致环化成吡唑的反应条件从肼和1,3-二羰基化合物的直接缩合到需要催化量的硫酸到过量硫酸的反应之间变化。在R ＝ CF 3的情况下，观察到区域选择性超出预期，这取决于反应条件。
• Heterocyclo-alkylsulfonyl pyrazole derivatives as anti-inflammatory/analgesic agents
  申请人：Pfizer Inc.

  公开号：US06531492B1

  公开（公告）日：2003-03-11

  The present invention relates to compounds of the formula wherein R2, R3, R6 and A are defined as in the specification, to pharmaceutical compositions containing them and to their medicinal use. The compounds of the invention are useful in the treatment or alleviation of inflammation and other inflammation associated disorders, such as osteoarthritis, rheumatoid arthritis, colon cancer and Alzheimer's disease, in mammals (preferably humans, dogs, cats and livestock).

  本发明涉及公式中R2、R3、R6和A如规范中定义的化合物，以及含有它们的药物组合物和它们的药用。本发明的化合物在治疗或缓解炎症和其他与炎症有关的疾病中有用，如骨关节炎、类风湿性关节炎、结肠癌和阿尔茨海默病，在哺乳动物（最好是人类、狗、猫和家畜）中。
• HETEROCYCLO-ALKYLSULFONYL PYRAZOLE DERIVATIVES AS ANTI-INFLAMMATORY/ANALGESIC AGENTS
  申请人：Pfizer Products Inc.

  公开号：EP1233959B1

  公开（公告）日：2005-03-16
• US6531492B1
  申请人：——

  公开号：US6531492B1

  公开（公告）日：2003-03-11
• [EN] HETEROCYCLO-ALKYLSULFONYL PYRAZOLE DERIVATIVES AS ANTI-INFLAMMATORY/ANALGESIC AGENTS<br/>[FR] DERIVE HETEROCYCLO-ALKYLSULFONYLE PYRAZOLE EN TANT QU'AGENTS ANTI-INFLAMMATOIRES/ANALGESIQUES
  申请人：PFIZER PROD INC

  公开号：WO2001040216A1

  公开（公告）日：2001-06-07

  The present invention relates to compounds of formula (I) wherein R?2, R3, R6¿ and A are defined as in the specification, to pharmaceutical compositions containing them and to their medicinal use. The compounds of the invention are useful in the treatment or alleviation of inflammation and other inflammation associated disorders, such as osteoarthritis, rheumatoid arthritis, colon cancer and Alzheimer's disease, in mammals (preferably humans, dogs, cats and livestock).