N-(3-chloro-4-fluorophenyl)benzenesulfonamide

• 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: N-(3-chloro-4-fluorophenyl)benzenesulfonamide
• 化学式: C₁₂H₉ClFNO₂S
• mdl: MFCD01213709
• 分子量: 285.726
• InChiKey: BWYPGLCNYADNPO-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：
  0.0
• 拓扑面积：
  54.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-(3-chloro-4-fluorophenyl)benzenesulfonamide 、 均三甲苯 在 碘苯二乙酸 作用下， 以 2,2,2-三氟乙醇 为溶剂， 反应 3.0h， 以56%的产率得到5-chloro-6-fluoro-1,2,4-trimethyl-9-(phenylsulfonyl)carbazole
  参考文献：
  名称：

  通过C–C / C–N键形成和烷基迁移合成咔唑的脱氢芳香环融合

  摘要：

  据报道，咔唑通过顺序的C–C / C–N键形成和选择性的烷基迁移而合成了分子间脱氢环化（IDA）。使用一锅操作中的高价碘（III）试剂PhI（OAc）2（PIDA），最多可实现5个C（sp2）–H键，1个N（sp3）–H键功能化和1个烷基（Me ，Et）组迁移都可以在环境实验室条件下由未预官能化的1,3,5-三烷基苯和苯胺类化合物实现。从机理上讲，它表明PIDA与苯甲酸酯反应生成氮离子或同等的碳正离子，这会影响第二个芳环被活化以形成C-C / C-N键。从战略上讲，描述了芳烃与苯胺的区域选择性融合。

  DOI：

  10.1021/acs.orglett.7b01117
• 作为产物：
  描述：

  苯磺酰氯 、 3-氯-4-氟苯胺 在 吡啶 作用下， 以 二氯甲烷 为溶剂， 以80 %的产率得到N-(3-chloro-4-fluorophenyl)benzenesulfonamide
  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

• Dehydrogenative Aromatic Ring Fusion for Carbazole Synthesis via C–C/C–N Bond Formation and Alkyl Migration
  作者：Saikat Maiti、Prasenjit Mal

  DOI：10.1021/acs.orglett.7b01117

  日期：2017.5.5

  reported. Using the hypervalent iodine(III) reagent PhI(OAc)2 (PIDA), in a one-pot operation, up to five C(sp2)–H bonds, one N(sp3)–H bond functionalization, and one alkyl (Me, Et) group migration could all be achieved from non-prefunctionalized 1,3,5-trialkylbenzenes and anilides under ambient laboratory conditions. Mechanistically, it is shown that PIDA reacts with anilides to generate a nitrenium ion

  据报道，咔唑通过顺序的C–C / C–N键形成和选择性的烷基迁移而合成了分子间脱氢环化（IDA）。使用一锅操作中的高价碘（III）试剂PhI（OAc）2（PIDA），最多可实现5个C（sp2）–H键，1个N（sp3）–H键功能化和1个烷基（Me ，Et）组迁移都可以在环境实验室条件下由未预官能化的1,3,5-三烷基苯和苯胺类化合物实现。从机理上讲，它表明PIDA与苯甲酸酯反应生成氮离子或同等的碳正离子，这会影响第二个芳环被活化以形成C-C / C-N键。从战略上讲，描述了芳烃与苯胺的区域选择性融合。
• 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.