{2-Methanesulfonyl-5-[5-(4-methoxy-phenyl)-3-trifluoromethyl-pyrazol-1-yl]-phenyl}-methanol | 304648-23-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: {2-Methanesulfonyl-5-[5-(4-methoxy-phenyl)-3-trifluoromethyl-pyrazol-1-yl]-phenyl}-methanol
• 英文别名: [5-[5-(4-methoxyphenyl)-3-(trifluoromethyl)pyrazol-1-yl]-2-methylsulfonylphenyl]methanol
• CAS: 304648-23-5
• 化学式: C₁₉H₁₇F₃N₂O₄S
• 分子量: 426.416
• InChiKey: GVPMWHQIUGWDCS-UHFFFAOYSA-N

物化性质

• 熔点：
  136-139 °C
• 沸点：
  616.4±55.0 °C(Predicted)
• 密度：
  1.39±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  29
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  89.8
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  {2-Methanesulfonyl-5-[5-(4-methoxy-phenyl)-3-trifluoromethyl-pyrazol-1-yl]-phenyl}-methanol 在 pyridinium chlorochromate 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 生成 2-(Methylsulfonyl)-5-[3-(trifluoromethyl)-5-(4-methoxyphenyl)-1H-pyrazole-1-yl]benzaldehyde
  参考文献：
  名称：

  Polar substitutions in the benzenesulfonamide ring of celecoxib afford a potent 1,5-diarylpyrazole class of COX-2 inhibitors

  摘要：

  Several chemical modifications in the N-1-benzenesulfonamide ring of celecoxib are presented. The series with a hydroxymethyl group adjacent to the sulfonamide was found to be the most potent modification that yielded many compounds selectively active against COX-2 enzyme in vitro. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2003.10.027
• 作为产物：
  描述：

  对甲氧基苯乙酮 在 sodium hydride 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 16.5h， 生成 {2-Methanesulfonyl-5-[5-(4-methoxy-phenyl)-3-trifluoromethyl-pyrazol-1-yl]-phenyl}-methanol
  参考文献：
  名称：

  Polar substitutions in the benzenesulfonamide ring of celecoxib afford a potent 1,5-diarylpyrazole class of COX-2 inhibitors

  摘要：

  Several chemical modifications in the N-1-benzenesulfonamide ring of celecoxib are presented. The series with a hydroxymethyl group adjacent to the sulfonamide was found to be the most potent modification that yielded many compounds selectively active against COX-2 enzyme in vitro. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2003.10.027

文献信息

• [EN] PYRAZOLES HAVING ANTIINFLAMMATORY ACTIVITY<br/>[FR] PYRAZOLES PRESENTANT UNE ACTIVITE ANTI-INFLAMMATOIRE
  申请人：REDDY RESEARCH FOUNDATION

  公开号：WO2000066562A1

  公开（公告）日：2000-11-09

  The present invention relates to novel antiinflammatory compounds, their derivatives, their analogs, their tautomeric forms, their stereoisomers, their regioisomers, their polymorphs, their pharmaceutically acceptable salts, their pharmaceutically acceptable solvates and pharmaceutically acceptable compositions containing them. More particularly, the present invention relates to novel heterocyclic compounds of general the formula (I), their derivatives, their analogs, their tautomeric forms, their stereoisomers, their regioisomers, their polymorphs, their pharmaceutically acceptable salts, their pharmaceutically acceptable solvates and pharmaceutically acceptable compositions containing them.

  本发明涉及新型抗炎化合物、它们的衍生物、类似物、互变异构体、立体异构体、区域异构体、多晶形态、药学上可接受的盐、药学上可接受的溶剂化合物以及含有它们的药学上可接受的组合物。更具体地说，本发明涉及一般式（I）的新型杂环化合物、它们的衍生物、类似物、互变异构体、立体异构体、区域异构体、多晶形态、药学上可接受的盐、药学上可接受的溶剂化合物以及含有它们的药学上可接受的组合物。
• Polar substitutions in the benzenesulfonamide ring of celecoxib afford a potent 1,5-diarylpyrazole class of COX-2 inhibitors
  作者：Sunil K. Singh、P.Ganapati Reddy、K.Srinivasa Rao、Braj B. Lohray、P. Misra、Shaikh A. Rajjak、Yeleswarapu K. Rao、A. Venkateswarlu

  DOI：10.1016/j.bmcl.2003.10.027

  日期：2004.1

  Several chemical modifications in the N-1-benzenesulfonamide ring of celecoxib are presented. The series with a hydroxymethyl group adjacent to the sulfonamide was found to be the most potent modification that yielded many compounds selectively active against COX-2 enzyme in vitro. (C) 2003 Elsevier Ltd. All rights reserved.
• Synthesis and SAR/3D-QSAR studies on the COX-2 inhibitory activity of 1,5-diarylpyrazoles to validate the modified pharmacophore
  作者：Sunil K. Singh、V. Saibaba、K. Srinivasa Rao、P. Ganapati Reddy、Pankaj R. Daga、S. Abdul Rajjak、Parimal Misra、Y. Koteswar Rao

  DOI：10.1016/j.ejmech.2005.03.016

  日期：2005.10

  Diverse analogs of 1,5-diarylpyrazoles having 3-hydroxymethyl-4-sulfamoyl (SO2NH2)/methyl sulfonyl (SO2Me)-pheny group at N-1 were synthesized and evaluated for their in vitro cyclooxygenase (COX-1/COX-2) inhibitory activity. The SAR study mainly involved the variations at positions C-3, C-5 and N-1 of the pyrazole ring. Several small hydrophobic groups at/around position-4 of C-5 phenyl, viz. 3,4-dimethylphenyl analog 9, 3-methyl-4-methylsulfanylphenyl analog 14 and 2,3-dihydrobenzo[b]thiophenyl analog 17, exhibited impressive COX-2 inhibitory potency. In general, the sulfonamide analogues with a CHF2 at C-3 were found to be more potent than those having a CF3 group. The three dimensional quantitative structure activity relationship comprising comparative molecular field analysis (3D-QSAR-CoMFA) afforded the models with high predictivity which further validated the acceptance of hydroxymethyl (CH2OH) group in the hydrophilic pocket of the COX-2 enzyme. (c) 2005 Elsevier SAS. All rights reserved.