4-fuoro-N-(4-(methylthio)phenyl)benzamide | 899010-93-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 4-fuoro-N-(4-(methylthio)phenyl)benzamide
• 英文别名: 4-fluoro-N-(4-(methylthio)phenyl)benzamide；4-fluoro-N-(4-methylsulfanylphenyl)benzamide
• CAS: 899010-93-6
• 化学式: C₁₄H₁₂FNOS
• mdl: MFCD09024048
• 分子量: 261.32
• InChiKey: OWWUTDWCERDITQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.071
• 拓扑面积：
  54.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-fuoro-N-(4-(methylthio)phenyl)benzamide 在 劳森试剂 作用下， 以 四氢呋喃 为溶剂， 以56%的产率得到N-(4-methylthiophenyl)-4-fluorothiobenzamide
  参考文献：
  名称：

  Synthesis, spasmolytic activity and structure–activity relationship study of a series of polypharmacological thiobenzanilides

  摘要：

  Recently we presented a series of benzanilide derivatives with a selective spasmolytic effect on terminal ileum preparations of the guinea pig. In this report we demonstrate a further development of these compounds. The exchange of the amide oxygen against a sulfur atom resulted in an up to 325 fold increase of the antispasmodic activity of the thiobenzanilide (IC50 of 0.1 mu M) compared to its benzanilide derivative. Considering their mode of action the compounds interacted with several molecular targets, suggesting that we identified a chemical identity able to modulate multiple targets simultaneously. Furthermore, based on this data set, we present a structure-activity relationship study supporting the important role of the sulfur atom. (C) 2010 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.ejps.2010.10.005
• 作为产物：
  描述：

  对氟苯甲酸 以 四氢呋喃 为溶剂， 反应 1.0h， 生成 4-fuoro-N-(4-(methylthio)phenyl)benzamide
  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

• Novel 5-substituted 1H-tetrazoles as cyclooxygenase-2 (COX-2) inhibitors
  作者：Baker Jawabrah Al-Hourani、Sai Kiran Sharma、Mavanur Suresh、Frank Wuest

  DOI：10.1016/j.bmcl.2012.01.093

  日期：2012.3

  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.
• Synthesis, spasmolytic activity and structure–activity relationship study of a series of polypharmacological thiobenzanilides
  作者：Gerda Brunhofer、Christian Studenik、Gerhard F. Ecker、Thomas Erker

  DOI：10.1016/j.ejps.2010.10.005

  日期：2011.1

  Recently we presented a series of benzanilide derivatives with a selective spasmolytic effect on terminal ileum preparations of the guinea pig. In this report we demonstrate a further development of these compounds. The exchange of the amide oxygen against a sulfur atom resulted in an up to 325 fold increase of the antispasmodic activity of the thiobenzanilide (IC50 of 0.1 mu M) compared to its benzanilide derivative. Considering their mode of action the compounds interacted with several molecular targets, suggesting that we identified a chemical identity able to modulate multiple targets simultaneously. Furthermore, based on this data set, we present a structure-activity relationship study supporting the important role of the sulfur atom. (C) 2010 Elsevier B.V. All rights reserved.