N-[4-(aminomethyl)phenyl]-4-methylbenzenesulfonamide | 926265-11-4

• 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-methylbenzenesulfonamide
• CAS: 926265-11-4
• 化学式: C₁₄H₁₆N₂O₂S
• 分子量: 276.359
• InChiKey: WVABMIXSFMSBMZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.14
• 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：

  N-[4-(aminomethyl)phenyl]-4-methylbenzenesulfonamide 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-methylbenzenesulfonamide
  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 吡啶 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 生成 N-[4-(aminomethyl)phenyl]-4-methylbenzenesulfonamide
  参考文献：
  名称：

  N-4-Substituted-benzyl-N′-tert-butylbenzyl thioureas as vanilloid receptor ligands: investigation on the role of methanesulfonamido group in antagonistic activity

  摘要：

  A series of N-4-substituted-benzyl-N'-tert-butylbenzyl thioureas were prepared for the study of their agonistic/antagonistic activities to the vanilloid receptor in rat DRG neurons. Their structure-activity relationship reveals that not only the two oxygens and amide hydrogen of sulfonamido group, but also the optimal size of methyl in methanesulfonamido group play an integral role for the antagonistic activity on vanilloid receptor. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2003.11.019

文献信息

• An Acid‐Controlled Method for the Regioselective Functionalization of Anilines over Aliphatic Amines
  作者：Bowen Li、Yulun Hu、Gregory P. Tochtrop

  DOI：10.1002/chem.202301336

  日期：2023.10.23

  Regioselective functionalization of anilines in the presence of aliphatic amines is illustrated utilizing classic conditions for the Baeyer-Mills reaction. Further, the defined principles of reactivity are shown to be broadly extended to other electrophiles.

  利用 Baeyer-Mills 反应的经典条件说明了在脂肪胺存在下苯胺的区域选择性官能化。此外，所定义的反应性原理被证明可以广泛扩展到其他亲电子试剂。