4-ethyl-N-(2-hydroxy-5-nitrophenyl)benzamide | 931412-28-1

• 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-ethyl-N-(2-hydroxy-5-nitrophenyl)benzamide
• 英文别名: 4-ethyl-N-(2-hydroxy-5-nitro-phenyl)benzamide
• CAS: 931412-28-1
• 化学式: C₁₅H₁₄N₂O₄
• 分子量: 286.287
• InChiKey: FXGJSMHZGPDOHD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  95.2
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-ethyl-N-(2-hydroxy-5-nitrophenyl)benzamide 在 palladium on activated charcoal 氢气 作用下， 以 乙醇 为溶剂， 以47%的产率得到N-(5-amino-2-hydroxy-phenyl)-4-ethyl-benzamide
  参考文献：
  名称：

  Synthesis and biological evaluation of new N-(2-hydroxy-4(or 5)-nitro/aminophenyl)benzamides and phenylacetamides as antimicrobial agents

  摘要：

  A new series of N-(2-hydroxy-4(or 5)-nitro/aminophenyl)benzamide and phenylacetamide derivatives (la-In, 2a-2n) were synthesized and evaluated for antibacterial and antifungal activities against Staphylococcus aureus, Bacillus subtilis, Klebsiella pneumoniae, Pseudomonas aeruginosa, Escherichia coli, Candida albicans, and their drug-resistant isolates. Microbiological results indicated that the compounds possessed a broad spectrum of activity against the tested microorganisms at MIC values between 500 and 1.95 mu g/ml. Benzamide derivative Id exhibited the greatest activity with MIC values of 1.95, 3.9, and 7.8 mu g/ml against drug-resistant B. subtilis, B. subtilis, and S. aureus, respectively. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2006.12.035
• 作为产物：
  描述：

  对乙基苯甲酸 在 氯化亚砜 、 碳酸氢钠 作用下， 以 乙醚 、 水 、 苯 为溶剂， 反应 3.0h， 生成 4-ethyl-N-(2-hydroxy-5-nitrophenyl)benzamide
  参考文献：
  名称：

  一些新型抗菌苯甲酰胺的合成和分子对接研究。

  摘要：

  常规抗生素的普遍使用已导致许多致病菌耐药菌株的出现。因此，我们旨在合成许多N-（2-羟基-（4或5）-硝基苯基）苯甲酰胺衍生物作为一类新型的抗菌化合物。此外，我们的第二个目标是在结合模式下预测活性结构与酶（DNA回转酶和FtsA）之间的相互作用。在这项研究中，合成了13种N-（2-羟基-（4或5-硝基苯基）-取代的苯甲酰胺，并用微量稀释法测定了它们的抗菌活性，根据这项工作，没有一种化合物显示出对念珠菌的任何活性。一些苯甲酰胺（4N1、5N1、5N2）对金黄色葡萄球菌和MSSA的活性非常显着，MIC值<4 µg / ml，即使发现它们比头孢他啶更有效。还发现4N1对粪肠球菌的临床分离株比庆大霉素更有效。分子对接研究表明，4N1、5N1和5N2与DNA陀螺酶具有良好的相互作用。而且，5N1也以结合模式与FtsA酶相互作用。只有化合物5N4对大肠杆菌ATCC 25922表现出非常好的活性。这些发

  DOI：

  10.1016/j.bioorg.2019.103368

文献信息

• FT-IR, FT-Raman, SERS spectra and computational calculations of 4-ethyl-<i>N</i>-(2′-hydroxy-5′-nitrophenyl)benzamide
  作者：C. Yohannan Panicker、Hema Tresa Varghese、L. Ushakumari、Tugba Ertan、Ilkay Yildiz、Carlos M. Granadeiro、Helena I. S. Nogueira、Y. Shyma Mary

  DOI：10.1002/jrs.2471

  日期：——

  Fourier transform infrared (FT-IR) and FT-Raman spectra of 4-ethyl-N-(2′-hydroxy-5′-nitrophenyl)benzamide were recorded and analyzed. A surface-enhanced Raman scattering (SERS) spectrum was recorded in silver colloid. The vibrational wavenumbers and corresponding vibrational assignments were examined theoretically using the Gaussian03 set of quantum chemistry codes. The red shift of the NH stretching wavenumber in the infrared spectrum from the computational wavenumber indicates the weakening of the NH bond resulting in proton transfer to the neighboring oxygen atom. The simultaneous IR and Raman activation of the CO stretching mode gives the charge transfer interaction through a π-conjugated path. The presence of methyl modes in the SERS spectrum indicates the nearness of the methyl group to the metal surface, which affects the orientation and metal molecule interaction. The first hyperpolarizability and predicted infrared intensities are reported. The calculated first hyperpolarizability is comparable with the reported values of similar derivatives and is an attractive subject for future studies of nonlinear optics. Optimized geometrical parameters of the title compound are in agreement with reported structures. Copyright © 2009 John Wiley & Sons, Ltd.

  记录并分析了 4-乙基-N-(2′-羟基-5′-硝基苯基)苯甲酰胺的傅立叶变换红外光谱（FT-IR）和傅立叶变换拉曼光谱。在银胶体中记录了表面增强拉曼散射（SERS）光谱。使用 Gaussian03 量子化学代码集对振动波文数和相应的振动赋值进行了理论研究。红外光谱中的 NH 拉伸波文数与计算波文数相比发生了红移，这表明 NH 键的减弱导致质子转移到了邻近的氧原子上。红外光谱和拉曼光谱同时激活了 CO 拉伸模式，表明电荷转移相互作用是通过 π 共轭路径进行的。SERS 光谱中出现的甲基模式表明甲基靠近金属表面，从而影响了取向和金属分子的相互作用。报告了第一超极化率和预测的红外强度。计算出的第一超极化率与报告中类似衍生物的值相当，是未来非线性光学研究的一个有吸引力的课题。标题化合物的优化几何参数与报道的结构一致。Copyright © 2009 John Wiley & Sons, Ltd. All Rights Reserved.
• Synthesis and molecular docking studies of some novel antimicrobial benzamides
  作者：Cemre Acar、Gozde Yalçın、Tuğba Ertan-Bolelli、Fatma Kaynak Onurdağ、Suzan Ökten、Funda Şener、İlkay Yıldız

  DOI：10.1016/j.bioorg.2019.103368

  日期：2020.1

  of classical antibiotics has caused to the growing emergence of many resistant strains of pathogenic bacteria. Therefore, we aimed to synthesize a number of N-(2-hydroxy-(4 or 5)-nitrophenyl)benzamide derivatives as a new class of antimicrobial compounds. Moreover, our second goal is to predict the interaction between active structures and enzymes (DNA -gyrase and FtsA) in the binding mode. In this study

  常规抗生素的普遍使用已导致许多致病菌耐药菌株的出现。因此，我们旨在合成许多N-（2-羟基-（4或5）-硝基苯基）苯甲酰胺衍生物作为一类新型的抗菌化合物。此外，我们的第二个目标是在结合模式下预测活性结构与酶（DNA回转酶和FtsA）之间的相互作用。在这项研究中，合成了13种N-（2-羟基-（4或5-硝基苯基）-取代的苯甲酰胺，并用微量稀释法测定了它们的抗菌活性，根据这项工作，没有一种化合物显示出对念珠菌的任何活性。一些苯甲酰胺（4N1、5N1、5N2）对金黄色葡萄球菌和MSSA的活性非常显着，MIC值<4 µg / ml，即使发现它们比头孢他啶更有效。还发现4N1对粪肠球菌的临床分离株比庆大霉素更有效。分子对接研究表明，4N1、5N1和5N2与DNA陀螺酶具有良好的相互作用。而且，5N1也以结合模式与FtsA酶相互作用。只有化合物5N4对大肠杆菌ATCC 25922表现出非常好的活性。这些发
• Synthesis and biological evaluation of new N-(2-hydroxy-4(or 5)-nitro/aminophenyl)benzamides and phenylacetamides as antimicrobial agents
  作者：Tugba Ertan、Ilkay Yildiz、Semiha Ozkan、Ozlem Temiz-Arpaci、Fatma Kaynak、Ismail Yalcin、Esin Aki-Sener、Ufuk Abbasoglu

  DOI：10.1016/j.bmc.2006.12.035

  日期：2007.3

  A new series of N-(2-hydroxy-4(or 5)-nitro/aminophenyl)benzamide and phenylacetamide derivatives (la-In, 2a-2n) were synthesized and evaluated for antibacterial and antifungal activities against Staphylococcus aureus, Bacillus subtilis, Klebsiella pneumoniae, Pseudomonas aeruginosa, Escherichia coli, Candida albicans, and their drug-resistant isolates. Microbiological results indicated that the compounds possessed a broad spectrum of activity against the tested microorganisms at MIC values between 500 and 1.95 mu g/ml. Benzamide derivative Id exhibited the greatest activity with MIC values of 1.95, 3.9, and 7.8 mu g/ml against drug-resistant B. subtilis, B. subtilis, and S. aureus, respectively. (c) 2007 Elsevier Ltd. All rights reserved.