4-amino-N-(4-methylbenzyl)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: 4-amino-N-(4-methylbenzyl)benzenesulfonamide
• 英文别名: N-(4-methylbenzyl)-4-aminobenzenesulfonamide；4-amino-N-[(4-methylphenyl)methyl]benzenesulfonamide
• 化学式: C₁₄H₁₆N₂O₂S
• 分子量: 276.359
• InChiKey: FMALNZIYCSTSQU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 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：

  4-phenylbenzoyl isothiocyanate 、 4-amino-N-(4-methylbenzyl)benzenesulfonamide 以 丙酮 为溶剂， 以60 mg的产率得到N-((4-(N-(4-methylbenzyl)sulfamoyl)phenyl)carbamothioyl)-[1,1'-biphenyl]-4-carboxamide
  参考文献：
  名称：

  Potent and selective N-(4-sulfamoylphenyl)thiourea-based GPR55 agonists

  摘要：

  To date, many known G protein-coupled receptor 55 (GPR55) ligands are those identified among the cannabinoids. In order to further study the function of GPR55, new potent and selective ligands are needed. In this study, we utilized the screening results from PubChem bioassay AID 1961 which reports the results of Image-based HIS for Selective Agonists of GPR55. Three compounds, CID1792579, CID1252842 and CID1011163, were further evaluated and used as a starting point to create a series of nanomolar potency GPR55 agonists with N-(4-sulfamoylphenyl)thiourea scaffold. The GPR55 activity of the compounds were screened by using a commercial beta-arrestin PathHunter assay and the potential compounds were further evaluated by using a recombinant HEK cell line exhibiting GPR55-mediated effects on calcium signalling. The designed compounds were not active when tested against various endocannabinoid targets (CB1R, CB2R, FAAH, MGL, ABHD6 and ABHD12), indicating compounds' selectivity for the GPR55. Finally, structure activity relationships of these compounds were explored. (C) 2015 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2015.10.050
• 作为产物：
  描述：

  N-(4-Methylbenzyl)-4-nitrobenzenesulfonamide 在 盐酸 、 tin 作用下， 以 乙醇 、 水 为溶剂， 以100%的产率得到4-amino-N-(4-methylbenzyl)benzenesulfonamide
  参考文献：
  名称：

  Potent and selective N-(4-sulfamoylphenyl)thiourea-based GPR55 agonists

  摘要：

  To date, many known G protein-coupled receptor 55 (GPR55) ligands are those identified among the cannabinoids. In order to further study the function of GPR55, new potent and selective ligands are needed. In this study, we utilized the screening results from PubChem bioassay AID 1961 which reports the results of Image-based HIS for Selective Agonists of GPR55. Three compounds, CID1792579, CID1252842 and CID1011163, were further evaluated and used as a starting point to create a series of nanomolar potency GPR55 agonists with N-(4-sulfamoylphenyl)thiourea scaffold. The GPR55 activity of the compounds were screened by using a commercial beta-arrestin PathHunter assay and the potential compounds were further evaluated by using a recombinant HEK cell line exhibiting GPR55-mediated effects on calcium signalling. The designed compounds were not active when tested against various endocannabinoid targets (CB1R, CB2R, FAAH, MGL, ABHD6 and ABHD12), indicating compounds' selectivity for the GPR55. Finally, structure activity relationships of these compounds were explored. (C) 2015 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2015.10.050

文献信息

• Cyclometalated palladium pre-catalyst for N-alkylation of amines using alcohols and regioselective alkylation of sulfanilamide using aryl alcohols
  作者：Ramesh Mamidala、Vanga Mukundam、Kunchala Dhanunjayarao、Krishnan Venkatasubbaiah

  DOI：10.1016/j.tet.2017.03.001

  日期：2017.4

  Simple pyrazole based palladacycle-phosphine with a high turnover has been developed and applied for the N-alkylation of amines and sulfanilamide using alcohols as substrates by hydrogen borrowing strategy. N-alkylation of primary and secondary amines resulted in high isolated yields at 100–130 °C, under solvent free conditions. More challenging secondary aliphatic as well as aromatic alcohols were

  已经开发出具有高周转率的简单的吡唑基四氢环磷酰胺，并将其用于通过醇借用策略以醇为底物的胺和磺胺的N-烷基化。在无溶剂条件下，伯胺和仲胺的N-烷基化可在100-130°C的条件下实现高分离产率。在相似的反应条件下，更具挑战性的仲脂族和芳族醇也成功地用作烷基化剂。使用苯甲醇对苯胺进行N-苄基化反应的周转数达到43000。值得注意的是，使用醇作为烷基化剂，已经实现了2-氨基苯并噻唑和4-氨基苯磺酰胺的区域选择性N-烷基化为相应的2-N-（烷基氨基）唑和4-氨基-（N-烷基）苯磺酰胺的区域选择性。 -膦系统。
• 一种合成氨基-(N-烷基)苯磺酰胺的方法
  申请人：南京理工大学

  公开号：CN106146358B

  公开（公告）日：2018-01-23

  本发明公开了一种合成氨基‑(N‑烷基)苯磺酰胺的方法。包括如下步骤：在反应容器中，加入氨基苯磺酰胺、铱络合物催化剂、碱、化合物醇、溶剂叔戊醇，反应混合物在120‑150 oC下反应数小时后，冷却到室温，旋转蒸发除去溶剂，然后通过柱分离，得到目标化合物。本发明使用商品化的氨基苯磺酰胺和近于无毒的化合物醇为起始原料；反应只生成水为副产物，无环境危害；反应原子经济性高。
• Effective Recognition of Different Types of Amino Groups: From Aminobenzenesulfonamides to Amino-(<i>N</i>-alkyl)benzenesulfonamides via Iridium-Catalyzed <i>N</i>-Alkylation with Alcohols
  作者：Lei Lu、Juan Ma、Panpan Qu、Feng Li

  DOI：10.1021/acs.orglett.5b00824

  日期：2015.5.15

  A simple, highly efficient, and general strategy for the direct synthesis of amino-(N-alkyl)benzenesulfonamides has been accomplished via direct N-alkylation of aminobenzenesulfonamides bearing both different types of amino groups with alcohols as alkylating agents. Notably, this research exhibited the potential for the recognition of different types of amino groups in the N-alkylation of complex molecules with alcohols, facilitating the progress of the transition-metal-catalyzed "hydrogen autotransfer (or hydrogen-borrowing) process.
• Selective N-Alkylation of Aminobenzenesulfonamides with Alcohols for the Synthesis of Amino-(N-alkyl)benzenesulfonamides Catalyzed by a Metal–Ligand Bifunctional Ruthenium Catalyst
  作者：Lu Shen、Xingliang Wu、Lili Shi、Xiangchao Xu、Jin Zhang、Feng Li

  DOI：10.1021/acs.joc.4c00166

  日期：2024.6.21