4-chloro-N,N-diphenylbenzenesulfonamide | 122685-91-0

• 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-chloro-N,N-diphenylbenzenesulfonamide
• 英文别名: 4-chloro-benzenesulfonic acid diphenylamide；4-Chlor-benzolsulfonsaeure-diphenylamid
• CAS: 122685-91-0
• 化学式: C₁₈H₁₄ClNO₂S
• 分子量: 343.834
• InChiKey: CLDVQAARJXVSEM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  45.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-chloro-N,N-diphenylbenzenesulfonamide 、 苯甲腈 在 正丁基锂 作用下， 生成 5-chloro-3-phenylbenzo[d]isothiazole 1,1-dioxide
  参考文献：
  名称：

  Ein bequemes Eintopfverfahren zur Synthese von 1,2-Benzisothiazol-1,1-dioxiden

  摘要：

  一种简便的一锅法用于合成1,2-苯异噻唑-1,1-二氧化物。正位锂化的N,N-二苯基苯磺酰胺6与芳香腈和N,N-二甲基氰脲酸酯反应，直接生成相应的3取代1,2-苯异噻唑-1,1-二氧化物8a-f。其他氰化合物仅转移氰基或其配体，生成o-取代苯磺酰胺9a-d。

  DOI：

  10.1055/s-1989-27263
• 作为产物：
  描述：

  4-氯苯磺酰氯 在 吡啶 、 cesium fluoride 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 6.0h， 生成 4-chloro-N,N-diphenylbenzenesulfonamide
  参考文献：
  名称：

  N,N‐Diarysulfonamide reduces proinflammatory cytokine interleukin‐6 levels in cells through nuclear factor‐κB regulation

  摘要：

  The synthesized sulfonamides were evaluated for cytotoxicity followed by the cytokine/inflammatory marker’s inhibition capability and its mechanism of action in RAW‐264.7 cells. Elevated interleukin‐6 (IL‐6) levels have been reported in inflammatory conditions and inflammation‐associated disorders. Hence, reducing the IL‐6 levels in inflammatory conditions can serve as an attractive therapeutic target in dealing the inflammation. Among 42 compounds, seven compounds showed significant inhibition of IL‐6 levels in lipopolysaccharide (LPS) challenged RAW‐264.7 cells at 12.5 µM concentration. Further, investigation revealed that the IC50 value of these compounds for reducing IL‐6 levels was found to be in the range of 9.7 to 2.6 µM. The promising compounds 5y (IC50 of 2.6 µM) and 5n (IC50 of 4.1 µM) along with other derivatives fulfil drug‐likeness parameters laid down by Lipinski’s rule of five. Further, analysis using RTqPCR and Western‐blot analysis revealed that treatment with 5n significantly reduced the expression of pro‐inflammatory, inflammatory and macrophage marker’s expression (IL‐1β, CCL2, COX2 and CD68) compared to LPS control. The mechanistic evaluation showed that RL‐442 exhibited anti‐inflammatory properties by modulating the nuclear factor‐κB (NF‐κB) activation. The identified compound can be a promising candidate for further discovery efforts to generate a preclinical candidate effective in inflammation.

  DOI：

  10.1002/cmdc.202300598

文献信息

• Ein bequemes Eintopfverfahren zur Synthese von 1,2-Benzisothiazol-1,1-dioxiden
  作者：D. Hellwinkel、R. Karle

  DOI：10.1055/s-1989-27263

  日期：——

  A Facile One-Pot Procedure for the Synthesis of 1,2-Benzisothiazole 1,1-Dioxides ortho-Lithiated N,N-diphenylbenzenesulfonamides 6 react with aromatic nitriles and N,N-dimethylcarbamonitrile, respectively, to give directly the corresponding 3-substituted 1,2-benzisothiazole-1,1-dioxides 8a-f. Other cyano compounds only transfer the cyano group or its ligands to generate the o-substituted benzenesulfonamides 9a-d.

  一种简便的一锅法用于合成1,2-苯异噻唑-1,1-二氧化物。正位锂化的N,N-二苯基苯磺酰胺6与芳香腈和N,N-二甲基氰脲酸酯反应，直接生成相应的3取代1,2-苯异噻唑-1,1-二氧化物8a-f。其他氰化合物仅转移氰基或其配体，生成o-取代苯磺酰胺9a-d。
• N,N‐Diarysulfonamide reduces proinflammatory cytokine interleukin‐6 levels in cells through nuclear factor‐κB regulation
  作者：Dattatraya Babar、Gopinath Khansole、Vishalkumar Singh、Akash Shinde、Vaishnavi Kambhampati、Sai Balaji Andugulapati、Haridas B. Rode

  DOI：10.1002/cmdc.202300598

  日期：——

  The synthesized sulfonamides were evaluated for cytotoxicity followed by the cytokine/inflammatory marker’s inhibition capability and its mechanism of action in RAW‐264.7 cells. Elevated interleukin‐6 (IL‐6) levels have been reported in inflammatory conditions and inflammation‐associated disorders. Hence, reducing the IL‐6 levels in inflammatory conditions can serve as an attractive therapeutic target in dealing the inflammation. Among 42 compounds, seven compounds showed significant inhibition of IL‐6 levels in lipopolysaccharide (LPS) challenged RAW‐264.7 cells at 12.5 µM concentration. Further, investigation revealed that the IC50 value of these compounds for reducing IL‐6 levels was found to be in the range of 9.7 to 2.6 µM. The promising compounds 5y (IC50 of 2.6 µM) and 5n (IC50 of 4.1 µM) along with other derivatives fulfil drug‐likeness parameters laid down by Lipinski’s rule of five. Further, analysis using RTqPCR and Western‐blot analysis revealed that treatment with 5n significantly reduced the expression of pro‐inflammatory, inflammatory and macrophage marker’s expression (IL‐1β, CCL2, COX2 and CD68) compared to LPS control. The mechanistic evaluation showed that RL‐442 exhibited anti‐inflammatory properties by modulating the nuclear factor‐κB (NF‐κB) activation. The identified compound can be a promising candidate for further discovery efforts to generate a preclinical candidate effective in inflammation.