N-(2,3-二甲基苯基)苯磺酰胺 | 126494-77-7

• 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: N-(2,3-二甲基苯基)苯磺酰胺
• 英文名称: 2,3-dimethyl-N-(phenylsulfonyl)aniline
• 英文别名: N-(2,3-dimethylphenyl)benzenesulfonamide
• CAS: 126494-77-7
• 化学式: C₁₄H₁₅NO₂S
• mdl: MFCD00091026
• 分子量: 261.345
• InChiKey: OXLUYOWIZVRQSU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.142
• 拓扑面积：
  54.6
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 海关编码：
  2935009090

反应信息

• 作为反应物：
  描述：

  N-(2,3-二甲基苯基)苯磺酰胺 在 氢氧化钾 、 溴苯 、 碘苯二乙酸 、 四丁基溴化铵 作用下， 以 甲醇 、 乙醚 为溶剂， 生成 2,3-dimethyl-4,4-dimethoxy-2,5-cyclohexadienone
  参考文献：
  名称：

  Synthesis and Spectroscopic Characterization of 1-13C- and 4-13C-Plastoquinone-9

  摘要：

  DOI：

  10.1002/1099-0690(200207)2002:13<2094::aid-ejoc2094>3.0.co;2-e
• 作为产物：
  描述：

  2-methoxycarbonyl-3-methyl-6-(trisopropylsilyl)aniline 在 吡啶 、 红铝 、 三氟乙酸 作用下， 以 正己烷 、 二氯甲烷 、 甲苯 为溶剂， 反应 8.0h， 生成 N-(2,3-二甲基苯基)苯磺酰胺
  参考文献：
  名称：

  Synthesis and Spectroscopic Characterization of 1-13C- and 4-13C-Plastoquinone-9

  摘要：

  DOI：

  10.1002/1099-0690(200207)2002:13<2094::aid-ejoc2094>3.0.co;2-e

文献信息

• Deconstructing Noncovalent Kelch-like ECH-Associated Protein 1 (Keap1) Inhibitors into Fragments to Reconstruct New Potent Compounds
  作者：Jakob S. Pallesen、Dilip Narayanan、Kim T. Tran、Sara M. Ø. Solbak、Giuseppe Marseglia、Louis M. E. Sørensen、Lars J. Høj、Federico Munafò、Rosa M. C. Carmona、Anthony D. Garcia、Haritha L. Desu、Roberta Brambilla、Tommy N. Johansen、Grzegorz M. Popowicz、Michael Sattler、Michael Gajhede、Anders Bach

  DOI：10.1021/acs.jmedchem.0c02094

  日期：2021.4.22

  Keap1–Nrf2 PPI inhibitors were dissected into 77 fragments in a fragment-based deconstruction reconstruction (FBDR) study and tested in four orthogonal assays. This gave 17 fragment hits of which six were shown by X-ray crystallography to bind in the Keap1 Kelch binding pocket. Two hits were merged into compound 8 with a 220–380-fold stronger affinity (Ki = 16 μM) relative to the parent fragments. Systematic

  靶向核因子类红细胞2相关因子2（Nrf2）和与Kelch样ECH相关蛋白1（Keap1）之间的蛋白相互作用是控制涉及氧化应激疾病的潜在治疗策略。在这里，在基于片段的解构重建（FBDR）研究中，将六类已知的小分子Keap1-Nrf2 PPI抑制剂分解为77个片段，并在四个正交试验中进行了测试。这给出了17个片段命中，其中X射线晶体学显示其中6个在Keap1 Kelch结合袋中结合。相对于亲本片段，两个命中片段以220-380倍的亲和力（K i = 16μM）被合并到化合物8中。系统优化产生了一些与K i有关的新颖类似物值0.04–0.5μM，通过X射线晶体学测定的结合模式，以及增强的微粒体稳定性。这证明了FBDR如何可用于发现新的片段片段，阐明重要的配体-蛋白质相互作用以及鉴定Keap1-Nrf2 PPI的新有效抑制剂。
• Hewson, Alan T.; Sharpe, David A.; Wadsworth, Alan H., Synthetic Communications, 1989, vol. 19, # 11-12, p. 2095 - 2100
  作者：Hewson, Alan T.、Sharpe, David A.、Wadsworth, Alan H.

  DOI：——

  日期：——
• HEWSON, ALAN T.;SHARPE, DAVID A.;WADSWORTH, ALAN H., SYNTH. COMMUN., 19,(1989) N1-12, C. 2095-2099
  作者：HEWSON, ALAN T.、SHARPE, DAVID A.、WADSWORTH, ALAN H.

  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.
• Synthesis and Spectroscopic Characterization of 1-13C- and 4-13C-Plastoquinone-9
  作者：Rutger B. Boers、Yolanda Pazos Randulfe、Hendrikus N. S. van der Haas、Marleen van Rossum-Baan、Johan Lugtenburg

  DOI：10.1002/1099-0690(200207)2002:13<2094::aid-ejoc2094>3.0.co;2-e

  日期：2002.7