(E)-4-(2-((2-hydroxybenzylidene)amino)ethyl)benzenesulfonamide | 869707-76-6

• 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: (E)-4-(2-((2-hydroxybenzylidene)amino)ethyl)benzenesulfonamide
• 英文别名: 4-(2-((2-hydroxybenzylidene)amino)ethyl)benzenesulfonamide
• CAS: 869707-76-6
• 化学式: C₁₅H₁₆N₂O₃S
• 分子量: 304.37
• InChiKey: XYIRQCSVYOCEFY-GZTJUZNOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  21.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  92.75
• 氢给体数：
  2.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (E)-4-(2-((2-hydroxybenzylidene)amino)ethyl)benzenesulfonamide 在 sodium tetrahydroborate 作用下， 以 甲醇 、 水 为溶剂， 反应 24.0h， 生成 4-(2-[(2-hydroxybenzyl)amino]ethyl)benzenesulfonamide
  参考文献：
  名称：

  Benzenesulfonamide derivatives as potent acetylcholinesterase, α-glycosidase, and glutathione S-transferase inhibitors: biological evaluation and molecular docking studies

  摘要：

  Sulfonamide derivatives exhibit a wide biological activity and can function as potential medical molecules in the development of a drug. Studies have reported that the compounds have an effect on many enzymes. In this study, the derivatives of amine sulfonamide (1i-11i) were prepared with reduced imine compounds (1-11) with NaBH4 in methanol. The synthesized compounds were fully characterized by spectral data and analytical. The effect of the synthesized derivatives on acetylcholinesterase (AChE), glutathione S-transferase (GST) and a-glycosidase (alpha-GLY) enzymes were determined. For the AChE and alpha-GLY, the most powerful inhibition was observed on 10 and 10i series with K-I value in the range 2.26 +/- 0.45-3.57 +/- 0.97 and 95.73 +/- 13.67-102.45 +/- 11.72 mu M, respectively. K-I values of the series for GST were found in the range of 22.76 +/- 1.23-49.29 +/- 4.49. Finally, the compounds have a stronger inhibitor in lower concentrations by the attachment of functional electronegative groups such as two halogens (-Br and -CI), -OH to the benzene ring and -SO2NH2. The crystal structures of AChE, alpha-GLY, and GST in complex with selected derivatives 4 and 10 show the importance of the functional moieties in the binding modes within the receptors.

  DOI：

  10.1080/07391102.2020.1790422
• 作为产物：
  描述：

  水杨醛 、 4-(2-氨乙基)苯磺酰胺 以 甲醇 为溶剂， 反应 6.0h， 以75%的产率得到(E)-4-(2-((2-hydroxybenzylidene)amino)ethyl)benzenesulfonamide
  参考文献：
  名称：

  新型定制苯磺酰胺衍生的席夫碱铜（II）嵌入复合物的结构阐明{光谱，单晶X射线衍射和计算DFT研究}：全面的生物学概况{DNA结合，pBR322 DNA裂解，拓扑I抑制和细胞毒活性}。

  摘要：

  从席夫碱支架HL1和HL2（E）-4-（2-（ （2-羟基-3-甲氧基亚苄基）氨基）乙基）苯磺酰胺和（E）-4-（2-（（（2-羟基亚苄基）氨基）乙基）苯磺酰胺。配合物1和2的结构阐明是通过采用各种光谱技术进行的，例如FT-IR，UV-vis，ESI-MS，EPR和单X射线晶体衍射研究。配合物1和2在单斜晶P21 / n和三斜晶P-1空间群中结晶，分别在Cu（II）周围具有与N，O-施主席夫碱配体配位的正方形平面几何形状。进行了复合物1和2的Hirshfeld表面分析，以确定不同的分子内和分子间非共价相互作用（H键，CH 3π等）。）负责稳定晶格。已经进行了基于密度泛函理论（B3LYP / DFT）的计算以获得前沿分子轨道的能量。复合物1和2与ct-DNA的体外结合特征比较采用多种生物物理技术进行了评估，即紫外可见，荧光，圆二色性和循环伏安法，这表明非共价插入结合模式具有更强烈的复合物1结

  DOI：

  10.1016/j.bioorg.2019.103427

文献信息

• Structure elucidation {spectroscopic, single crystal X-ray diffraction and computational DFT studies} of new tailored benzenesulfonamide derived Schiff base copper(II) intercalating complexes: Comprehensive biological profile {DNA binding, pBR322 DNA cleavage, Topo I inhibition and cytotoxic activity}
  作者：Zeenat Afsan、Thierry Roisnel、Sartaj Tabassum、Farukh Arjmand

  DOI：10.1016/j.bioorg.2019.103427

  日期：2020.1

  suggested non-covalent intercalative binding mode with more avid binding propensity of complex 1 compared to complex 2. The cleavage experiments of complex 1 was performed by gel electrophoretic assay which revealed efficient cleavage mediated via oxidative pathway. Furthermore, topoisomerase I enzymatic activity of complex 1 was carried out employing gel electrophoretic assay which demonstrated significant

  从席夫碱支架HL1和HL2（E）-4-（2-（ （2-羟基-3-甲氧基亚苄基）氨基）乙基）苯磺酰胺和（E）-4-（2-（（（2-羟基亚苄基）氨基）乙基）苯磺酰胺。配合物1和2的结构阐明是通过采用各种光谱技术进行的，例如FT-IR，UV-vis，ESI-MS，EPR和单X射线晶体衍射研究。配合物1和2在单斜晶P21 / n和三斜晶P-1空间群中结晶，分别在Cu（II）周围具有与N，O-施主席夫碱配体配位的正方形平面几何形状。进行了复合物1和2的Hirshfeld表面分析，以确定不同的分子内和分子间非共价相互作用（H键，CH 3π等）。）负责稳定晶格。已经进行了基于密度泛函理论（B3LYP / DFT）的计算以获得前沿分子轨道的能量。复合物1和2与ct-DNA的体外结合特征比较采用多种生物物理技术进行了评估，即紫外可见，荧光，圆二色性和循环伏安法，这表明非共价插入结合模式具有更强烈的复合物1结
• Transition metal complexes (M=Cu, Ni and Mn) of Schiff-base ligands: Syntheses, crystal structures, and inhibitory bioactivities against urease and xanthine oxidase
  作者：Yu-Guang Li、Da-Hua Shi、Hai-Liang Zhu、Hong Yan、Seik Weng Ng

  DOI：10.1016/j.ica.2007.02.019

  日期：2007.6

  Six new transition metal complexes (M=Cu(II), Ni(II) and Mn(III)) of tridentate (H2L1, HL2) and/or bidentate (HL3, HL4) Schiff-base ligands, obtained from the condensation of salicylaldehyde with glycine, N-(2-aminoethyl)morpholine, 4-(2-aminoethyl)phenylic acid and 4-(2-aminoethyl)benzsulfamide, respectively, were synthesized and structurally determined by single-crystal X-ray analysis. Complexes 1-6 were evaluated for their effect on the jack bean urease and xanthine oxidase (XO). Copper(II) complexes 1-3 (IC50=0.43-2.25 mu M) showed potent inhibitory activity against jack bean urease, comparable with acetohydroxamicacid (IC50=42.12 mu M), which is a positive reference. And these copper(II) complexes (IC50=10.26-15.82 mu M) also exhibited strong ability to inhibit activity of XO, comparable to allopurinol (IC50=10.37 mu M), which was used as a positive reference. Nickel(II) and manganese(III) complexes 4-6 showed weak inhibitory activity to jack bean urease (IC50=4.36-8.25 mu M) and no ability to inhibit XO (IC50>100 mu M). (C) 2007 Elsevier B.V. All rights reserved.
• Benzenesulfonamide derivatives as potent acetylcholinesterase, α-glycosidase, and glutathione S-transferase inhibitors: biological evaluation and molecular docking studies
  作者：Parham Taslimi、Mesut Işık、Fikret Türkan、Mustafa Durgun、Cüneyt Türkeş、İlhami Gülçin、Şükrü Beydemir

  DOI：10.1080/07391102.2020.1790422

  日期：2021.10.13

  Sulfonamide derivatives exhibit a wide biological activity and can function as potential medical molecules in the development of a drug. Studies have reported that the compounds have an effect on many enzymes. In this study, the derivatives of amine sulfonamide (1i-11i) were prepared with reduced imine compounds (1-11) with NaBH4 in methanol. The synthesized compounds were fully characterized by spectral data and analytical. The effect of the synthesized derivatives on acetylcholinesterase (AChE), glutathione S-transferase (GST) and a-glycosidase (alpha-GLY) enzymes were determined. For the AChE and alpha-GLY, the most powerful inhibition was observed on 10 and 10i series with K-I value in the range 2.26 +/- 0.45-3.57 +/- 0.97 and 95.73 +/- 13.67-102.45 +/- 11.72 mu M, respectively. K-I values of the series for GST were found in the range of 22.76 +/- 1.23-49.29 +/- 4.49. Finally, the compounds have a stronger inhibitor in lower concentrations by the attachment of functional electronegative groups such as two halogens (-Br and -CI), -OH to the benzene ring and -SO2NH2. The crystal structures of AChE, alpha-GLY, and GST in complex with selected derivatives 4 and 10 show the importance of the functional moieties in the binding modes within the receptors.