N-(4,6-dimethylpyrimidin-2-yl)-4-[(2-hydroxybenzylidene)amino]benzene sulfonamide | 16182-36-8

• 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-(4,6-dimethylpyrimidin-2-yl)-4-[(2-hydroxybenzylidene)amino]benzene sulfonamide
• 英文别名: N-(4,6-dimethylpyrimidin-2-yl)-4-[(2-hydroxybenzylidene)amino]benzenesulfonamide；N-(4,6-dimethylpyrimidin-2-yl)-4-[(2-hydroxyphenyl)methylideneamino]benzenesulfonamide
• CAS: 16182-36-8
• 化学式: C₁₉H₁₈N₄O₃S
• 分子量: 382.443
• InChiKey: ITDUYWAXGRRWSH-UHFFFAOYSA-N

物化性质

• 沸点：
  628.9±65.0 °C(Predicted)
• 密度：
  1.33±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  27
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  113
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  N-(4,6-dimethylpyrimidin-2-yl)-4-[(2-hydroxybenzylidene)amino]benzene sulfonamide 、 二氯二氧化钼 以 乙酸乙酯 为溶剂， 生成
  参考文献：
  名称：

  Abramenko; Sergienko, Russian Journal of Inorganic Chemistry, 2002, vol. 47, # 6, p. 806 - 815

  摘要：

  DOI：
• 作为产物：
  描述：

  在 硫酸 作用下， 以 水 为溶剂， 生成 N-(4,6-dimethylpyrimidin-2-yl)-4-[(2-hydroxybenzylidene)amino]benzene sulfonamide
  参考文献：
  名称：

  Selective coordination ability of sulfamethazine Schiff-base ligand towards copper(II): Molecular structures, spectral and SAR study

  摘要：

  In the present work, a combined experimental and theoretical study of the N-(4,6-Dimethyl-pyrimidin-2-yl)-4-[(2-hydroxy-benzylidene)amino]benzenesulfonamide ligand (H2L) and its mononuclear and magnetically diluted binuclear Cu-II complexes has been performed using IR, TG/DTA, magnetic, EPR, and conductivity measurements. Calculated g-tensor values showed best agreement with experimental values from EPR when carried out using the MPW1PW91 functional. Coordination of H2L to a Cu-II center, regardless of the binding site and Cu:L stoichiometry, leads to a significant decrease in the antibacterial activity compared to the free ligand as well as reference drugs in the case of Staphylococcus aureus. Structural-activity relationship suggests that E-LUMO, Delta E, dipole moment, polarizability and electrophilicity index were the most significant descriptors for the correlation with the antibacterial activity. (C) 2013 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.saa.2013.12.066

文献信息

• Hydrogen-bond effect, spectroscopic and molecular structure investigation of sulfamethazine Schiff-base: Experimental and quantum chemical calculations
  作者：Ahmed M. Mansour、Nour T. Abdel Ghani

  DOI：10.1016/j.molstruc.2013.02.028

  日期：2013.5

  Abstract Comprehensive theoretical and experimental structural studies on N-(4,6-dimethyl-pyrimidin-2-yl)-4-[(2-hydroxy-benzylidene)-amino]benzenesulfonamide (SMS) have been carried out by elemental analysis, FT IR, 1 H NMR, UV–Vis. and MS. Optimized molecular structure and harmonic vibrational frequencies have been investigated by DFT/B3LYP and HF methods combined with 6-31G(d) basis set. Stability

  摘要 通过元素分析、FT 对 N-(4,6-二甲基-嘧啶-2-基)-4-[(2-羟基-亚苄基)-氨基]苯磺酰胺 (SMS) 进行了全面的理论和实验结构研究。红外、 1 H 核磁共振、紫外-可见光。和女士。已通过 DFT/B3LYP 和 HF 方法结合 6-31G(d) 基组研究了优化的分子结构和谐波振动频率。分子的稳定性源于超共轭相互作用、电荷离域和分子内氢键已使用自然键轨道 (NBO) 分析进行了分析。通过TD-DFT方法讨论了电子结构，并确定了前沿分子轨道的描述和电子密度的重定位。1 H NMR 化学位移是通过规范不变原子轨道 (GIAO) 方法在气体和 DMSO 介质中计算的，使用极化连续介质模型 (PCM)。构效关系已被用于将生物活性与一些适当的量子描述符相关联，例如 E HOMO 、E LUMO 、能隙、偶极矩 ( μ )、整体硬度 ( η )、柔软度 ( S )、亲电指数 ( ω
• Schiff bases derived from 4-amino-N-substituted benzenesulfonamide: synthesis, spectral characterisation and MIC evaluation
  作者：G. Valarmathy、R. Subbalakshmi、B. Sabarika、C. Nisha

  DOI：10.4314/bcse.v35i2.16

  日期：——

  ABSTRACT. The present study is aimed to synthesise Schiff bases from sulfathiazole/ sulfamethoxazole/ sulfadimidine with 2-hydroxybenzaldehyde. The synthesized Schiff bases were characterized by analytical data, IR, 1H-NMR, 13C-NMR, UV-Vis spectra, mass spectra and screened for antibacterial activity against gram positive bacteria Staphylococcus aureus and gram negative bacteria Salmonella typhiand antifungal activity against Candida albicans and Mucor by disc diffusion method. Zone of inhibition indicated that the Schiff base possessed highly potent antimicrobial activity when compared to sulpha drugs.                     KEY WORDS: 4-Amino-N-(1,3-thiazol-2-yl)benzenesulfonamide, 4-amino-N-(5-methylisoxazol-3-yl)-benzenesulfonamide, 4-amino-N-(4,6-dimethylpyrimidin-2-yl)benzenesulfonamide, 2-hydroxybenzaldehyde, antimicrobial activity   Bull. Chem. Soc. Ethiop. 2021, 35(2), 435-448.  DOI: https://dx.doi.org/10.4314/bcse.v35i2.16

  摘要：本研究旨在合成来自磺胺嘧啶/磺胺甲氧苄啶/磺胺二甲嘧啶和2-羟基苯甲醛的席夫碱。合成的席夫碱通过分析数据、红外、1H-NMR、13C-NMR、UV-Vis光谱、质谱进行表征，并通过盘扩散法对革兰氏阳性细菌金黄色葡萄球菌和革兰氏阴性细菌伤寒沙门氏菌以及白色念珠菌和粘液菌的抗菌活性进行筛选。抑菌区域表明与磺胺类药物相比，席夫碱具有高效的抗微生物活性。                     关键词：4-氨基-N-(1,3-噻唑-2-基)苯磺酰胺，4-氨基-N-(5-甲基异噁唑-3-基)-苯磺酰胺，4-氨基-N-(4,6-二甲基嘧啶-2-基)苯磺酰胺，2-羟基苯甲醛，抗微生物活性   《埃塞俄比亚化学学会会报》2021年第35卷第2期，435-448。DOI: https://dx.doi.org/10.4314/bcse.v35i2.16

• Thermal and spectral studies on Co(II), Ni(II) and Cu(II) complexes of sulfamethazine Schiff base
  作者：M. Gaber、H.E. Mabrouk、Y.M. Shaibi、A.A. Ba-Issa

  DOI：10.1016/0040-6031(92)80139-n

  日期：1992.10

  The thermal behavior of sulfamethazine Schiff base complexes with Co(II), Ni(II) and Cu(II) ions has been studied. The thermal stability of these complexes is discussed in terms of the type of metal ions. The energies of activation were determined and discussed in relation to the structure of the complex which is characterized by elemental analysis and IR spectra.
• Fluorophosphoric Acid Promoted Formation of Imines of Sulfonamides and Dihydropyridines at Room Temperature
  作者：Vikas B. Suryawanshi、Sujit S. Mathakari、Mantosh B. Swami、Sushil R. Mathapati

  DOI：10.1080/00304948.2023.2238097

  日期：2024.3.3
• Abramenko; Sergienko, Russian Journal of Inorganic Chemistry, 2002, vol. 47, # 6, p. 806 - 815
  作者：Abramenko、Sergienko

  DOI：——

  日期：——