3-((4-isopropylbenzyl)amino)benzenesulfonamide

• 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: 3-((4-isopropylbenzyl)amino)benzenesulfonamide
• 英文别名: 3-[(4-Propan-2-ylphenyl)methylamino]benzenesulfonamide
• 化学式: C₁₆H₂₀N₂O₂S
• 分子量: 304.413
• InChiKey: ULXIJGLBKMFPLN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  80.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-((4-isopropylbenzyl)amino)benzenesulfonamide 、 1-溴-三氟对二甲苯 在 potassium carbonate 作用下， 以 乙腈 为溶剂， 反应 0.5h， 以46%的产率得到3-((4-isopropylbenzyl)(4-(trifluoromethyl)benzyl)amino)benzenesulfonamide
  参考文献：
  名称：

  Discovery of new benzensulfonamide derivatives as tripedal STAT3 inhibitors

  摘要：

  Persistent activated STAT3 has a striking correlation with cancer development and inhibition of STAT3 signaling pathway is a novel therapeutic way for human cancers. Among STAT family, STAT1 and STAT3 play opposite roles in tumorigenesis. However, the discovery of selective STAT3 inhibitors is still challenging to date. In this study, a series of small-molecular (MW < 500) benzensulfanilamide derivatives were designed to selectively suppress STAT3 activation for anti-cancer treatment. The most potent compound 11 inhibited both overexpressed and IL-6 induced STAT3 phosphorylation, whereas 11 displayed little effect on the phosphorylation of other STAT isoforms STAT1, STAT5, demonstrating 11 was a selective STAT3 inhibitor. Meanwhile, 11 dismissed STAT3 DNA binding activity and colony formation. In addition, 11 elevated the ROS level and induced apoptosis of cancer cells. Furthermore, 11 effectively suppressed tumor growth in an in vivo mouse-xenograft model. (C) 2018 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2018.03.053
• 作为产物：
  描述：

  间氨基苯磺酰胺 、 4-异丙基苯甲醛 在 溶剂黄146 、 三乙酰氧基硼氢化钠 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 以96%的产率得到3-((4-isopropylbenzyl)amino)benzenesulfonamide
  参考文献：
  名称：

  Discovery of new benzensulfonamide derivatives as tripedal STAT3 inhibitors

  摘要：

  Persistent activated STAT3 has a striking correlation with cancer development and inhibition of STAT3 signaling pathway is a novel therapeutic way for human cancers. Among STAT family, STAT1 and STAT3 play opposite roles in tumorigenesis. However, the discovery of selective STAT3 inhibitors is still challenging to date. In this study, a series of small-molecular (MW < 500) benzensulfanilamide derivatives were designed to selectively suppress STAT3 activation for anti-cancer treatment. The most potent compound 11 inhibited both overexpressed and IL-6 induced STAT3 phosphorylation, whereas 11 displayed little effect on the phosphorylation of other STAT isoforms STAT1, STAT5, demonstrating 11 was a selective STAT3 inhibitor. Meanwhile, 11 dismissed STAT3 DNA binding activity and colony formation. In addition, 11 elevated the ROS level and induced apoptosis of cancer cells. Furthermore, 11 effectively suppressed tumor growth in an in vivo mouse-xenograft model. (C) 2018 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2018.03.053