4-甲氧基-N,N-二苯基苯磺酰胺 | 94257-09-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 4-甲氧基-N,N-二苯基苯磺酰胺
• 英文名称: N,N-diphenyl-4-methoxybenzenesulfonamide
• 英文别名: 4-Methoxy-benzolsulfonsaeure-diphenylamid；4-methoxy-benzenesulfonic acid diphenylamide；4-methoxy-N,N-diphenyl-benzenesulfonamide；4-methoxy-N,N-diphenylbenzenesulfonamide
• CAS: 94257-09-7
• 化学式: C₁₉H₁₇NO₃S
• 分子量: 339.415
• InChiKey: MJWOAYUDFMVLJZ-UHFFFAOYSA-N

物化性质

• 熔点：
  122-123 °C
• 沸点：
  494.1±47.0 °C(Predicted)
• 密度：
  1.268±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  55
• 氢给体数：
  0
• 氢受体数：
  4

安全信息

• 海关编码：
  2935009090

反应信息

• 作为反应物：
  描述：

  4-甲氧基-N,N-二苯基苯磺酰胺 、 苯甲腈 在 正丁基锂 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以58%的产率得到5-methoxy-3-phenylbenzo[d]isothiazole 1,1-dioxide
  参考文献：
  名称：

  Rommel, Michael; Fukuzumi, Takeo; Bode, Jeffrey W., Journal of the American Chemical Society, 2008, vol. 130, p. 17266 - 17267

  摘要：

  DOI：
• 作为产物：
  描述：

  2-溴苯酚 在 正丁基锂 、 cesium fluoride 作用下， 以 四氢呋喃 、 正己烷 、 乙腈 为溶剂， 反应 6.0h， 生成 4-甲氧基-N,N-二苯基苯磺酰胺
  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

• Facile <i>N</i>-Arylation of Amines and Sulfonamides and <i>O</i>-Arylation of Phenols and Arenecarboxylic Acids
  作者：Zhijian Liu、Richard C. Larock

  DOI：10.1021/jo0602221

  日期：2006.4.1

  An efficient, transition-metal-free procedure for the N-arylation of amines, sulfonamides, and carbamates and O-arylation of phenols and carboxylic acids has been achieved by allowing these substrates to react with a variety of o-silylaryl triflates in the presence of CsF. Good to excellent yields of arylated products are obtained under very mild reaction conditions. This chemistry readily tolerates

  通过使这些底物在存在下与多种邻甲硅烷基芳基三氟甲磺酸酯反应，已实现了一种有效的，无过渡金属的胺，磺酰胺和氨基甲酸酯的N-芳基化以及酚和羧酸的O-芳基化方法。的CsF。在非常温和的反应条件下，芳基化产物的收率好至极好。这种化学反应易于耐受各种官能团。
• Ni(cod)(duroquinone)-Catalyzed C–N Cross-Coupling for the Synthesis of <i>N</i>,<i>N</i>-Diarylsulfonamides
  作者：Tian You、Junqi Li

  DOI：10.1021/acs.orglett.2c02670

  日期：2022.9.16

  We report a C–N cross-coupling reaction of weakly nucleophilic N-arylsulfonamides and aryl bromides to access N,N-diarylsulfonamides using Ni(cod)(DQ) as a catalyst without additional ligands. The process is compatible with electron-deficient and electron-rich aryl and heteroaryl bromides (34 examples, 21–98%) and can be applied to the derivatization of an N-arylsulfonamide pharmaceutical compound

  我们报告了弱亲核性N-芳基磺酰胺和芳基溴化物的 C-N 交叉偶联反应，使用 Ni(cod)(DQ) 作为催化剂，无需额外的配体即可获得N , N-二芳基磺酰胺。该工艺与缺电子和富电子的芳基和杂芳基溴化物兼容（34 个例子，21-98%），可用于N-芳基磺酰胺药物化合物的衍生化。
• Almasi; Serban, Academia Republicii Populare Romine, Filiala Cluj, Studii si Cercetari de Chimie, 1956, vol. 7, p. 141 - 149
  作者：Almasi、Serban

  DOI：——

  日期：——
• Rommel, Michael; Fukuzumi, Takeo; Bode, Jeffrey W., Journal of the American Chemical Society, 2008, vol. 130, p. 17266 - 17267
  作者：Rommel, Michael、Fukuzumi, Takeo、Bode, Jeffrey W.

  DOI：——

  日期：——
• 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.