N-(4-acetylphenyl)-2-nitrobenzenesulfonamide | 63228-71-7

• 英文名称: N-(4-acetylphenyl)-2-nitrobenzenesulfonamide
• CAS: 63228-71-7
• 化学式: C₁₄H₁₂N₂O₅S
• 分子量: 320.326
• InChiKey: HFHBTHIQCKLBSF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  117
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  N-(4-acetylphenyl)-2-nitrobenzenesulfonamide 在 phenyltrimethylammonium tribromide 作用下， 以 四氢呋喃 为溶剂， 反应 12.0h， 生成
  参考文献：
  名称：

  Discovery and structure-activity relationship of novel 4-hydroxy-thiazolidine-2-thione derivatives as tumor cell specific pyruvate kinase M2 activators

  摘要：

  Pyruvate kinase M2 isoform (PKM2) is a crucial protein responsible for aerobic glycolysis of cancer cells. Activation of PKM2 may alter aberrant metabolism in cancer cells. In this study, we discovered a 4-hydroxy-thiazolidine-2-thione compound 2 as a novel PKM2 activator from a random screening of an in-house compound library. Then a series of novel 4-hydroxy-thiazolidine-2-thione derivatives were designed and synthesized for screening as potent PKM2 activators. Among these, some compounds showed higher PKM2 activation activity than lead compound 2 and also exhibited significant anti proliferative activities on human cancer cell lines at nanomolar concentration. The compound 5w was identified as the most potent antitumor agent, which showed excellent anti-proliferative effects with IC50 values from 0.46 mu M to 0.81 mu M against H1299, HCT116, Hela and PC3 cell lines. 5w also showed less cytotoxicity in non-tumor cell line HELF compared with cancer cells. In addition, Preliminary pharmacological studies revealed that 5w arrests the cell cycle at the G2/M phase in HCT116 cell line. The best PKM2 activation by compound 5t was rationalized through docking studies. (C) 2017 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2017.11.023
• 作为产物：
  描述：

  4-氨基苯乙酮 、 邻硝基苯磺酰氯 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 生成 N-(4-acetylphenyl)-2-nitrobenzenesulfonamide
  参考文献：
  名称：

  无过渡金属的串联环化/ N-芳基化反应：一种通过双自由基途径获得联芳基苏丹酰胺衍生物的方法。

  摘要：

  报道了一种新的芳烃与1,2,3,4-苯并噻三嗪-1,1-二氧化物的无过渡金属串联环化/ N-芳基化反应序列的程序。该反应通过分子内均质环化反应生成N–H联芳基杜仲中间体，这使得芳烃插入可以以高收率获得各种官能化的联芳基杜仲衍生物。机理研究表明，均相环化是由双自由基物质执行的，该自由基是由1,2,3,4-苯并噻三嗪-1,1-二氧化物的热分解引发的，从而释放出氮分子。

  DOI：

  10.1021/acs.orglett.0c02393