1-(4-(methylsulfonyl)phenyl)-5-phenyl-1H-tetrazole

• 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-(methylsulfonyl)phenyl)-5-phenyl-1H-tetrazole
• 英文别名: 1-(4-Methylsulfonylphenyl)-5-phenyltetrazole
• 化学式: C₁₄H₁₂N₄O₂S
• 分子量: 300.341
• InChiKey: VVZOVHDNUPFYLB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  86.1
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  1-(4-(methylthio)phenyl)-5-phenyl-1H-tetrazole 在 oxone 作用下， 反应 3.0h， 生成 1-(4-(methylsulfonyl)phenyl)-5-phenyl-1H-tetrazole
  参考文献：
  名称：

  Novel 5-substituted 1H-tetrazoles as cyclooxygenase-2 (COX-2) inhibitors

  摘要：

  A series of novel 5-substituted 1H-tetrazoles as cyclooxygenase-2 (COX-2) inhibitors was prepared via treatment of various diaryl amides with tetrachlorosilane/sodium azide. All compounds were tested in cyclooxygenase (COX) assays in vitro to determine COX-1 and COX-2 inhibitory potency and selectivity. Tetrazoles contained a methylsulfonyl or sulfonamide group as COX-2 pharmacophore displayed only low inhibitory potency towards COX-2. Most potent compounds showed IC50 values of 6 and 7 mu M for COX-2. All compounds showed IC50 values greater 100 mu M for COX-1 inhibition. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.01.093

文献信息

• 1,2-Diarylimidazoles as Potent, Cyclooxygenase-2 Selective, and Orally Active Antiinflammatory Agents
  作者：Ish K. Khanna、Richard M. Weier、Yi Yu、Xiang D. Xu、Francis J. Koszyk、Paul W. Collins、Carol M. Koboldt、Amy W. Veenhuizen、William E. Perkins、Jacquelen J. Casler、Jaime L. Masferrer、Yan Y. Zhang、Susan A. Gregory、Karen Seibert、Peter C. Isakson

  DOI：10.1021/jm9700225

  日期：1997.5.1

  Series of 1,2-diarylimidazoles has been synthesized and found to contain highly potent and selective inhibitors of the human COX-2 enzyme. The paper describes a short synthesis of the target 1,2-diarylimidazoles starting with aryl nitriles. Different portions of the diarylimidazole (I) were modified to establish SAR. Systematic variations of the substituents in the aryl ring B have yielded very potent (IC50 = 10-100 nm) and selective (1000-12500) inhibitors of the COX-2 enzyme. The study on the influence of substituents in the imidazole ring established that a CF3 group at position 4 gives the optimum oral activity. A number of the diarylimidazoles showed excellent inhibition in the adjuvant induced arthritis model (e.g., ED50 = 0.02 mph for 22 and 34). The diarylimidazoles are also potent inhibitors of carrageenan-induced edema (ED50 = 9-30 mph) sind hyperalgesia (ED50 = 11-40 mpk). Several orally active diarylimidazoles show no GI toxicity in the rat and mouse up to 200 mpk.