4-Methoxy-N-pyridin-3-yl-benzenesulfonamide | 736936-81-5

• 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-Methoxy-N-pyridin-3-yl-benzenesulfonamide
• 英文别名: 4-methoxy-N-pyridin-3-ylbenzenesulfonamide
• CAS: 736936-81-5
• 化学式: C₁₂H₁₂N₂O₃S
• 分子量: 264.305
• InChiKey: YXRDIJMPRVTEQX-UHFFFAOYSA-N

物化性质

• 溶解度：
  >39.6 [ug/mL]

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  76.7
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  3-溴吡啶 、 对甲氧基苯磺酰胺 在 copper(l) iodide 、 potassium carbonate 、 1,3-二(2-吡啶基)-1,3-丙二酮 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 36.0h， 以54%的产率得到4-Methoxy-N-pyridin-3-yl-benzenesulfonamide
  参考文献：
  名称：

  Cross coupling of 3-bromopyridine and sulfonamides (R1NHSO2R2·R1=H, Me, alkyl; R2=alkyl and aryl) catalyzed by CuI/1,3-di(pyridin-2-yl)propane-1,3-dione

  摘要：

  N-(3-Pyridinyl)-substituted secondary and tertiary sulfonamides have been synthesized in good to excellent yields by the reaction of 3-bromopyridine with primary and secondary alkyl and aryl sulfonamides (MeSO2NH2, MeSO2NHMe, TolSO(2)NH(2), TolSO(2)NHMe, 1,3-propanesultam, and 1,4-butanesultam), catalyzed by CuI (20 mol %) and 1,3-di(pyridin-2-yl)propane-1,3-dione (20 mol %) with K2CO3 (200 mol %) in DMF (0.17 M for ArBr) at 110-120 degrees C over 36-40 h. 2-Bromopyridine, 4-bromopyridine, and a wide variety of substituted phenyl bromides can also be successfully coupled with sulfonamides under these reaction conditions. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2009.11.037

文献信息

• Discovery of 4-methoxy-N-(1-naphthyl)benzenesulfonamide derivatives as small molecule dual-target inhibitors of tubulin and signal transducer and activator of transcription 3 (STAT3) based on ABT-751
  作者：Xuebao Wang、Ying Lu、Doudou Sun、Jinheng Qian、Sijun Tu、Weixia Yue、Humin Lin、Haijie Tang、Fanxi Meng、Qin He、Zixin Xie、Yuan Zhang、Huijun Chen、Shumei Ma、Zhigui Zuo、Faqing Ye

  DOI：10.1016/j.bioorg.2022.105864

  日期：2022.8

  site to inhibit tubulin polymerization with IC50 values 0.83 μM, but also directly bound to STAT3 protein to inhibit STAT3 phosphorylation with IC50 value of 6.84 μM. Three other compounds (TG03, DL15, and DL16) also inhibit this phosphorylation. In terms of single target inhibition, DL14 is slightly inferior to positive drugs, but it shows a good anti-tumor effect in vivo, and can inhibit >80% of

  过度表达的微管蛋白和持续激活的 STAT3 在许多癌症的发展中发挥着重要作用，是潜在的治疗靶点。基于β-微管蛋白抑制剂ABT-751设计并优化了一系列4-甲氧基-N-(1-萘)苯磺酰胺衍生物，以验证STAT3和微管蛋白双靶点抑制剂是否具有更好的抗肿瘤效果。化合物DL14在体外对A549、MDA-MB-231和HCT-116细胞表现出较强的抑制活性，IC 50值分别为1.35 μM、2.85 μM和3.04 μM。进一步实验表明，DL14不仅竞争性地结合秋水仙碱结合位点抑制微管蛋白聚合，IC 50值为0.83 μM，而且直接与STAT3蛋白结合抑制STAT3磷酸化，IC 50值为6.84 μM。其他三种化合物（TG03、DL15 和 DL16）也抑制这种磷酸化。在单靶点抑制方面，DL14略逊于阳性药物，但在体内表现出良好的抗肿瘤作用，可抑制>80%的异种移植肿瘤生长。这项研究描述了一种新型的
• Cross coupling of 3-bromopyridine and sulfonamides (R1NHSO2R2·R1=H, Me, alkyl; R2=alkyl and aryl) catalyzed by CuI/1,3-di(pyridin-2-yl)propane-1,3-dione
  作者：Xiaojun Han

  DOI：10.1016/j.tetlet.2009.11.037

  日期：2010.1

  N-(3-Pyridinyl)-substituted secondary and tertiary sulfonamides have been synthesized in good to excellent yields by the reaction of 3-bromopyridine with primary and secondary alkyl and aryl sulfonamides (MeSO2NH2, MeSO2NHMe, TolSO(2)NH(2), TolSO(2)NHMe, 1,3-propanesultam, and 1,4-butanesultam), catalyzed by CuI (20 mol %) and 1,3-di(pyridin-2-yl)propane-1,3-dione (20 mol %) with K2CO3 (200 mol %) in DMF (0.17 M for ArBr) at 110-120 degrees C over 36-40 h. 2-Bromopyridine, 4-bromopyridine, and a wide variety of substituted phenyl bromides can also be successfully coupled with sulfonamides under these reaction conditions. (C) 2009 Elsevier Ltd. All rights reserved.