[1-(4-Methylsulfonylphenyl)-5-phenylpyrazol-3-yl]methyl methanesulfonate | 443920-01-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: [1-(4-Methylsulfonylphenyl)-5-phenylpyrazol-3-yl]methyl methanesulfonate
• 英文别名: [1-(4-methylsulfonylphenyl)-5-phenylpyrazol-3-yl]methyl methanesulfonate
• CAS: 443920-01-2
• 化学式: C₁₈H₁₈N₂O₅S₂
• 分子量: 406.483
• InChiKey: UBGJDFPVJGQGJQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  27
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  112
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  [1-(4-Methylsulfonylphenyl)-5-phenylpyrazol-3-yl]methyl methanesulfonate 在 sodium azide 、 palladium 10% on activated carbon 、 氢气 、 三乙胺 作用下， 以 1,4-二氧六环 、 水 、 乙酸乙酯 、 N,N-二甲基甲酰胺 为溶剂， 反应 14.0h， 生成 1-[1-(4-methanesulfonylphenyl)-5-phenyl-1H-pyrazol-3-ylmethyl]-3-(3-trifluoromethylphenyl)urea
  参考文献：
  名称：

  Synthesis and Structure−Activity Relationship Studies of Urea-Containing Pyrazoles as Dual Inhibitors of Cyclooxygenase-2 and Soluble Epoxide Hydrolase

  摘要：

  A series of dual inhibitors containing a 1,5-diarylpyrazole and a urea were designed, synthesized, and evaluated as novel COX-2/sEH dual:inhibitors in vitro using recombinant enzyme assays and in vivo using a lipopolysaccharide (LPS) induced model of pain in rats. The best inhibition potencies and selectivity for sEH and COX-2 over COX-1 were obtained with compounds (21b, 211, and 21j) in which both the 1,5-diaryl-pyrazole group aid the urea group are linked with a three-methylene group. Compound 21i showed the best pharmacokinetic profiles in both mice and rats (higher AUC and longer half life). Following subcutaneous administration at 10 mg/kg, compound 21i exhibited antiallodynic activity that is more effective than the same dose of either a COX-2 inhibitor (celecoxib) or a sEH inhibitor (t-AUCB) alone, as well as coadministration of:both inhibitors. Thus, these novel dual inhibitors exhibited enhanced in vivo antiallodynic activity in a nociceptive behavioral assay.

  DOI：

  10.1021/jm2001376
• 作为产物：
  描述：

  4-苯基-2,4-二氧丁酸乙酯 在 lithium aluminium tetrahydride 、 溶剂黄146 、 三乙胺 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 为溶剂， 生成 [1-(4-Methylsulfonylphenyl)-5-phenylpyrazol-3-yl]methyl methanesulfonate
  参考文献：
  名称：

  Synthesis and Activity of a New Methoxytetrahydropyran Derivative as Dual Cyclooxygenase-2/5-Lipoxygenase Inhibitor

  摘要：

  Dual COX-2/5-LO inhibitors are described as potential new therapeutic agents for inflammatory diseases. A surprisingly potent effect of a 5-LO pharmacophoric group on the COX-2 inhibition is presented as well as pharmacological in vitro and in vivo results. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(02)00013-6