N-(4-(aminomethyl)phenyl)-4-fluorobenzenesulfonamide | 926196-94-3

• 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: N-(4-(aminomethyl)phenyl)-4-fluorobenzenesulfonamide
• 英文别名: N-[4-(aminomethyl)phenyl]-4-fluorobenzenesulfonamide
• CAS: 926196-94-3
• 化学式: C₁₃H₁₃FN₂O₂S
• 分子量: 280.323
• InChiKey: AENANPZVKPPRHQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  19
• 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：
  80.6
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N-(4-(aminomethyl)phenyl)-4-fluorobenzenesulfonamide 在 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成 N-[4-[[(2-(methylamino)quinazolin-4-yl)amino]methyl]phenyl]-4-fluorobenzenesulfonamide
  参考文献：
  名称：

  Design, Synthesis, and Biological Evaluation of New Diaminoquinazolines as β-Catenin/Tcf4 Pathway Inhibitors

  摘要：

  More than 50 new diaminoquinazoline derivatives have been synthesized and evaluated in a colon carcinoma cell growth inhibition assay using HCT116 and SW480 cells. Twenty compounds with good cell growth inhibitory activities (<4 mu M) were tested as inhibitors of the beta-catenin/T cell transcription factor 4 (Tcf4) signaling pathway using a HCT116 cell-based luciferase reporter assay. Results from the biological activities as well as the comparative molecular field analysis (CoMFA) of the properties of the molecules yielded a preliminary structure-activity relationship (SAR). Three potent compounds, 74, 78, and 86, showed IC50 values <1 mu M for growth inhibition of HCT116 cells and similar to 1 mu M for SW480 cells, as well as IC50 values of 1.5-2.5 mu M for HCT116 cells with the luciferase reporter assay.

  DOI：

  10.1021/jm201494a
• 作为产物：
  描述：

  4-(N-BOC-氨甲基)苯胺 在 三乙胺 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 生成 N-(4-(aminomethyl)phenyl)-4-fluorobenzenesulfonamide
  参考文献：
  名称：

  Design, Synthesis, and Biological Evaluation of New Diaminoquinazolines as β-Catenin/Tcf4 Pathway Inhibitors

  摘要：

  More than 50 new diaminoquinazoline derivatives have been synthesized and evaluated in a colon carcinoma cell growth inhibition assay using HCT116 and SW480 cells. Twenty compounds with good cell growth inhibitory activities (<4 mu M) were tested as inhibitors of the beta-catenin/T cell transcription factor 4 (Tcf4) signaling pathway using a HCT116 cell-based luciferase reporter assay. Results from the biological activities as well as the comparative molecular field analysis (CoMFA) of the properties of the molecules yielded a preliminary structure-activity relationship (SAR). Three potent compounds, 74, 78, and 86, showed IC50 values <1 mu M for growth inhibition of HCT116 cells and similar to 1 mu M for SW480 cells, as well as IC50 values of 1.5-2.5 mu M for HCT116 cells with the luciferase reporter assay.

  DOI：

  10.1021/jm201494a

文献信息

• Nitro-sulfinate Reductive Coupling to Access (Hetero)aryl Sulfonamides
  作者：Sandra E. Gatarz、Oliver M. Griffiths、Henrique A. Esteves、Wenhua Jiao、Peter Morse、Ethan L. Fisher、David C. Blakemore、Steven V. Ley

  DOI：10.1021/acs.joc.3c02557

  日期：2024.2.2

  A method to assemble (hetero)aryl sulfonamides via the reductive coupling of aryl sulfinates and nitroarenes is reported. Various reducing conditions with sodium bisulfite and with or without tin(II) chloride in DMSO were developed using an ultrasound bath to improve reaction homogeneity and mixing. A range of (hetero)aryl sulfonamides bearing a selection of functional groups were prepared, and the

  报道了一种通过芳基亚磺酸盐和硝基芳烃的还原偶联组装（杂）芳基磺酰胺的方法。使用超声波浴开发了在 DMSO 中使用亚硫酸氢钠以及含或不含氯化锡 (II) 的各种还原条件，以改善反应均匀性和混合。制备了一系列带有精选官能团的（杂）芳基磺酰胺，并研究了转化机制。这些研究使我们提出了亚硝基芳烃中间体的形成，这是通过独立的分子偶联策略建立的。