N-(4-acetylphenyl)-2-bromobenzenesulfonamide

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: N-(4-acetylphenyl)-2-bromobenzenesulfonamide
• 化学式: C₁₄H₁₂BrNO₃S
• 分子量: 354.224
• InChiKey: QMEUYHYABZGOKL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  20
• 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：
  71.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-(4-acetylphenyl)-2-bromobenzenesulfonamide 在 sodium formate 作用下， 以 二甲基亚砜 为溶剂， 反应 10.0h， 以65%的产率得到9-acetyl-6H-dibenzo[c,e][1,2]thiazine 5,5-dioxide
  参考文献：
  名称：

  使用 DMSO/HCOONa·2H2O 系统对 2-溴苯磺酰胺进行分子内芳基化：获得二苯并磺胺

  摘要：

  在 DMSO 中用 HCOONa·2H 2 O 处理N-芳基-或N-苄基-2-卤代苯磺酰胺后合成了六元或七元二苯磺胺，而无需使用额外的措施和添加剂，例如光照射、电化学装置、过渡金属、和氧化剂。所得二苯并磺胺的游离 NH 基团的进一步官能化证明了该方法的合成实用性。

  DOI：

  10.1002/adsc.202200140
• 作为产物：
  描述：

  2-溴苯磺酰氯 、 4-氨基苯乙酮 在 吡啶 作用下， 反应 2.0h， 生成 N-(4-acetylphenyl)-2-bromobenzenesulfonamide
  参考文献：
  名称：

  使用 DMSO/HCOONa·2H2O 系统对 2-溴苯磺酰胺进行分子内芳基化：获得二苯并磺胺

  摘要：

  在 DMSO 中用 HCOONa·2H 2 O 处理N-芳基-或N-苄基-2-卤代苯磺酰胺后合成了六元或七元二苯磺胺，而无需使用额外的措施和添加剂，例如光照射、电化学装置、过渡金属、和氧化剂。所得二苯并磺胺的游离 NH 基团的进一步官能化证明了该方法的合成实用性。

  DOI：

  10.1002/adsc.202200140

文献信息

• 含嘌呤环的苯磺酰胺查尔酮类衍生物、其制备方法及用途
  申请人：贵州大学

  公开号：CN108892668A

  公开（公告）日：2018-11-27

  本发明公开了一种含嘌呤环的苯磺酰胺查尔酮类衍生物、其制备方法及用途，具有以下的通式（I）：式中：R1为4‑氧甲基、4‑叔丁基、4‑甲基、4‑氟、4‑氯、4‑溴、2‑甲基、2‑氟、2‑氯、2‑溴、和氢原子；R2为甲基、乙基、苄基。本发明能抑制抗烟草花叶病毒、黄瓜花叶病毒和马铃薯Y病毒和南方水稻黑条矮缩病毒的含嘌呤环。
• Antiviral properties and interaction of novel chalcone derivatives containing a purine and benzenesulfonamide moiety
  作者：Dagui Zhou、Dandan Xie、Fangcheng He、Baoan Song、Deyu Hu

  DOI：10.1016/j.bmcl.2018.04.042

  日期：2018.6

  A new concise and facile method was explored to synthesize a series of novel chalcone derivatives containing a purine and benzenesulfonamide moiety and their antiviral properties were evaluated against TMV and CMV. Biological assays indicated that several of the derivatives exhibited significant anti-TMV and anti-CMV activities in vivo. In particular, compound d2 displayed excellent inactivating activity against TMV, with the EC50 value of 51.65 mu g/mL, which was better than that of ribavirin (150.45 mu g/mL). Molecular docking showed that there are four hydrogen bonds between compound d2 and TMV coat protein (TMV-CP). Compound d2 demonstrated strong binding capacity to TMV-CP with K-a = 1.58 x 10(5) L/mol and K-d = 12.16 mu M. These findings indicated that chalcone derivatives are worthy of further research and development as templates for new antiviral agents. (C) 2018 Elsevier Ltd. All rights reserved.
• Discovery and structure-activity relationship of novel 4-hydroxy-thiazolidine-2-thione derivatives as tumor cell specific pyruvate kinase M2 activators
  作者：Ridong Li、Xianling Ning、Shuo Zhou、Zhiqiang Lin、Xingyu Wu、Hong Chen、Xinyu Bai、Xin Wang、Zemei Ge、Runtao Li、Yuxin Yin

  DOI：10.1016/j.ejmech.2017.11.023

  日期：2018.1

  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.
• Intramolecular Arylation of 2‐Bromobenzenesulfonamides Using DMSO/HCOONa ⋅ 2H ₂ O System: An Access To Dibenzosultams
  作者：Feiyue Hao、Guyue Liu、Zhengneng Jin、Guoliang Dai、Nagatoshi Nishiwaki、Jiashou Wu

  DOI：10.1002/adsc.202200140

  日期：2022.6.7

  Six- or seven-membered dibenzosultams were synthesized upon treatment of N-aryl- or N-benzyl-2-halobenzenesulfonamides with HCOONa ⋅ 2H2O in DMSO without using additional measures and additives, such as light irradiation, electrochemical apparatus, transition metals, and oxidants. Further functionalization of the free NH group of the resultant dibenzosultams demonstrates the synthetic practicability

  在 DMSO 中用 HCOONa·2H 2 O 处理N-芳基-或N-苄基-2-卤代苯磺酰胺后合成了六元或七元二苯磺胺，而无需使用额外的措施和添加剂，例如光照射、电化学装置、过渡金属、和氧化剂。所得二苯并磺胺的游离 NH 基团的进一步官能化证明了该方法的合成实用性。