N-(4-fluorobenzyl)-4-nitrobenzenesulfonamide

• 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-fluorobenzyl)-4-nitrobenzenesulfonamide
• 英文别名: N-[(4-fluorophenyl)methyl]-4-nitrobenzenesulfonamide
• 化学式: C₁₃H₁₁FN₂O₄S
• 分子量: 310.306
• InChiKey: HIZSKUVTRKAHCS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  21
• 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：
  100
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  N-(4-fluorobenzyl)-4-nitrobenzenesulfonamide 在 盐酸 、 tin 作用下， 以 乙醇 、 水 为溶剂， 以88%的产率得到4-amino-N-(4-fluorobenzyl)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
• 作为产物：
  描述：

  对氟苄胺 、 对硝基苯磺酰氯 在 吡啶 作用下， 以 二氯甲烷 为溶剂， 以63%的产率得到N-(4-fluorobenzyl)-4-nitrobenzenesulfonamide
  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

• Base‐Promoted Michael Addition/Smiles Rearrangement/ <i>N</i> ‐Arylation Cascade: One‐Step Synthesis of 1,2,3‐Trisubstituted 4‐Quinolones from Ynones and Sulfonamides
  作者：Jing Liu、Dan Ba、Weiwei Lv、Yanhui Chen、Zemin Zhao、Guolin Cheng

  DOI：10.1002/adsc.201900960

  日期：2020.1.7

  synthesize 1,2,3‐trisubstituted 4‐quinolones from readily available ynones and sulfonamides was developed. The construction of one C−C bond and two C−N bonds via cleavage of one N−S, one C−S, and one C−X (X=F, Cl, Br, O) bond is achieved under transition‐metal‐free conditions in one step. This transformation generates 1 equiv. of sulfur dioxide and 1 equiv. of hydrogen halide as the byproducts. The broad substrate

  已开发了一种通用，实用且环保的方案，可以从容易获得的炔酮和磺酰胺中合成1,2,3-三取代的4-喹诺酮。在过渡金属的作用下，通过裂解一个N-S，一个C-S和一个C-X（X = F，Cl，Br，O）键，可以构建一个C-C键和两个C-N键。一步就能达到无条件。此变换生成1个当量。二氧化硫和1当量 卤化氢作为副产物。1,2,3-三取代的4-喹诺酮类化合物的52个实例证明了广泛的底物范围和官能团耐受性。初步的机理研究支持顺序的迈克尔加成/微笑重排/ N芳基化反应途径。
• 10.1021/jacs.4c03826
  作者：Sedikides, Alexi T.、Lennox, Alastair J. J.

  DOI：10.1021/jacs.4c03826

  日期：——

  Monofluoroalkenes are stable and lipophilic amide bioisosteres used in medicinal chemistry. However, efficient and stereoselective methods for synthesizing Z-monofluoroalkenes are underdeveloped. We envisage (Z)-β-fluoro-vinyl iodonium salts (Z-FVIs) as coupling partners for the diverse and stereoselective synthesis of Z-monofluoroalkenes. Disclosed herein is the development and application of a silver(I)-catalyzed

  单氟烯烃是用于药物化学的稳定且亲脂的酰胺生物等排体。然而，用于合成Z-单氟烯烃的有效且立体选择性的方法尚未开发。我们设想(Z) -β-氟乙烯基碘鎓盐 ( Z -FVI) 作为偶联伙伴，用于Z -单氟烯烃的多样化和立体选择性合成。本文公开了银(I)催化方法的开发和应用，用于在一步中从炔烃获得具有独特的Z-立体选择性和区域选择性的广泛( Z )-FVI。实验和计算研究深入了解催化循环的机制和银 (I) 催化剂的作用，并通过几种立体定向衍生化探索 ( Z )-FVI 的反应性。
• Potent and selective N-(4-sulfamoylphenyl)thiourea-based GPR55 agonists
  作者：Sari Yrjölä、Teija Parkkari、Dina Navia-Paldanius、Tuomo Laitinen、Agnieszka A. Kaczor、Tarja Kokkola、Frank Adusei-Mensah、Juha R. Savinainen、Jarmo T. Laitinen、Antti Poso、Amy Alexander、June Penman、Lisa Stott、Marie Anskat、Andrew J. Irving、Tapio J. Nevalainen

  DOI：10.1016/j.ejmech.2015.10.050

  日期：2016.1

  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.