4-(4-methoxy-2-nitrophenylamino)-4-oxobutanoic acid

• 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-(4-methoxy-2-nitrophenylamino)-4-oxobutanoic acid
• 英文别名: 4-(2-nitro-4-methoxyphenylamino)-4-oxobutanoic acid；4-(4-Methoxy-2-nitroanilino)-4-oxobutanoic acid
• 化学式: C₁₁H₁₂N₂O₆
• mdl: MFCD00425565
• 分子量: 268.226
• InChiKey: DBBWQXIPXFGNTL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.82
• 重原子数：
  19.0
• 可旋转键数：
  6.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.272
• 拓扑面积：
  118.77
• 氢给体数：
  2.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  4-(4-methoxy-2-nitrophenylamino)-4-oxobutanoic acid 在 碳酸氢钠 作用下， 以 水 为溶剂， 生成 sodium N-[(2-methoxyphenyl)]-4-oxo-4-[oxyl]butanamide
  参考文献：
  名称：

  基于羧酸盐配体的 5 配位有机锡 (IV) 配合物的合成、表征和生物学筛选

  摘要：

  摘要 本文重点研究了基于羧酸盐配体4-((4-甲氧基-2-硝基苯基)氨基)-4-氧代丁酸的三种5-配位Sn(IV)配合物的合成。该配合物在固态（FT-IR、单晶 XRD 和微元素分析）和溶液态（1H、13C 和 119Sn NMR）中均进行了表征，结果表明配体的羧酸根部分与 Sn 相连原子。5 配位三角双锥结构是从晶体学数据获得的报告复合物与理想结构有一点点失真。初步抗真菌筛选表明，如众所周知的抗真菌药物特比萘芬所示，受试化合物具有 100% 的真菌抑制能力。抑菌结果表明，与市售的标准抗菌药物头孢克肟和罗克霉素相比，这些化合物对多种病原体具有突出的抑制能力。针对 H157 癌细胞系的抗增殖/抗癌结果显示，化合物 1 和 2 显示出最大的活性（即使在 2 μg/mL 终浓度下也具有 49-69% 的细胞毒性）。发现测试化合物对人角膜上皮细胞 (HCEC) 具有活性。合成的化合物对HCEC几乎无毒。当以

  DOI：

  10.1016/j.molstruc.2020.127683
• 作为产物：
  描述：

  丁二酸酐 、 2-硝基-4-甲氧基苯胺 在 溶剂黄146 作用下， 以90%的产率得到4-(4-methoxy-2-nitrophenylamino)-4-oxobutanoic acid
  参考文献：
  名称：

  Synthesis, spectroscopic characterization and in vitro antimicrobial, anticancer and antileishmanial activities as well interaction with Salmon sperm DNA of newly synthesized carboxylic acid derivative, 4-(4-methoxy-2-nitrophenylamino)-4-oxobutanoic acid

  摘要：

  This paper stresses on the synthesis, characterization of novel carboxylic acid derivative and its application in pharmaceutics. Carboxylic acid derivatives have a growing importance in medicine, particularly in oncology. A novel carboxylic acid, 4-(4-methoxy-2-nitrophenylamino)-4-oxobutanoic acid, was synthesized and characterized by elemental analysis, FT-IR, NMR (H-1, and C-13), mass spectrometry and single crystal X-ray structural analysis. The structure of the title compound, C11H12N2O6, shows the molecules dimerised by short intramolecular O-H center dot center dot center dot O hydrogen bonds. The compound was screened for in vitro antimicrobial, anticancer, and antileishmanial activities as well as interaction with SS-DNA. The compound was also checked for in vitro anticancer activity against BHK-21, H-157 and HCEC cell lines, and showed significant anticancer activity. The compound was almost non-toxic towards human corneal epithelial cells (HCEC) and did not show more than 7.4% antiproliferative activity when used at the 2.0 mu g/mL end concentration. It was also tested for antileishmanial activity against the promastigote form of leishmania major and obtained attractive result. DNA interaction study exposes that the binding mode of the compound with SS-DNA is an intercalative as it results in hypochromism along with minor red shift. A new and efficient strategy to identify pharmacophores sites in carboxylic acid derivative for antibacterial/antifungal activity using Petra, Osiris and Molinspiration (POM) analyses was also carried out. (C) 2014 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.saa.2014.11.061

文献信息

• Facile esterification of carboxylic acids with organophosphorus reagents
  作者：V. Balasubramaniyan、V.G. Bhatia、S.B. Wagh

  DOI：10.1016/s0040-4020(01)88552-5

  日期：1983.1

  A mixture of alkyl phosphate esters (APE) obtained from P4O10 and alkanols taken in 1:6 mole ratio is an excellent esterification reagent for several classes of carboxylic acids. This new reagent offers several advantages compared to conventional reagents.

  由P 4 O 10获得的烷基磷酸酯（APE）和以1：6摩尔比获得的链烷醇的混合物是用于几类羧酸的优良酯化试剂。与常规试剂相比，这种新试剂具有多个优点。
• Synthesis, characterization and biological screenings of 5-coordinated Organotin(IV) complexes based on carboxylate ligand
  作者：Muhammad Sirajuddin、Saqib Ali、Vickie McKee、Abdul Matin

  DOI：10.1016/j.molstruc.2020.127683

  日期：2020.4

  Abstract This article focus on the synthesis of three 5-coordinated Sn(IV) complexes based on carboxylate ligand: 4-((4-methoxy-2-nitrophenyl)amino)-4-oxobutanoic acid. The complexes were characterized both in solid state (FT-IR, single crystal XRD and micro elemental analysis) as well as in solution state (1H, 13C and 119Sn NMR) and their results demonstrate that the carboxylate moiety of the ligand

  摘要 本文重点研究了基于羧酸盐配体4-((4-甲氧基-2-硝基苯基)氨基)-4-氧代丁酸的三种5-配位Sn(IV)配合物的合成。该配合物在固态（FT-IR、单晶 XRD 和微元素分析）和溶液态（1H、13C 和 119Sn NMR）中均进行了表征，结果表明配体的羧酸根部分与 Sn 相连原子。5 配位三角双锥结构是从晶体学数据获得的报告复合物与理想结构有一点点失真。初步抗真菌筛选表明，如众所周知的抗真菌药物特比萘芬所示，受试化合物具有 100% 的真菌抑制能力。抑菌结果表明，与市售的标准抗菌药物头孢克肟和罗克霉素相比，这些化合物对多种病原体具有突出的抑制能力。针对 H157 癌细胞系的抗增殖/抗癌结果显示，化合物 1 和 2 显示出最大的活性（即使在 2 μg/mL 终浓度下也具有 49-69% 的细胞毒性）。发现测试化合物对人角膜上皮细胞 (HCEC) 具有活性。合成的化合物对HCEC几乎无毒。当以
• Prospective Application of Two New Pyridine-Based Zinc (II) Amide Carboxylate in Management of Alzheimer’s Disease: Synthesis, Characterization, Computational and in vitro Approaches
  作者：Rehman Zafar、Humaira Naureen、Muhammad Zubair、Khadija Shahid、Muhammad Saeed Jan、Samar Akhtar、Hammad Ahmad、Wajeeha Waseem、Ali Haider、Saqib Ali、Muhammad Tariq、Abdul Sadiq

  DOI：10.2147/dddt.s311619

  日期：——

  complexes which were potentially analyzed for various biological applications like acetylcholinesterase (AChE), butyrylcholinesterase (BChE) inhibitory potentials, and antioxidant assays. Computational docking studies also simulated results to understand the interactions. Additionally, thermodynamic parameters utilizing molecular dynamic simulation were performed to determine the ligand protein stability

  背景：阿尔茨海默病 (AD) 是一种主要由痴呆症描述的神经退行性疾病。尽管阿尔茨海默病已为人所知一个多世纪，但它的起源仍然是个谜，研究人员正在探索许多治疗方案，包括胆碱酯酶技术。乙酰胆碱 ACh 神经递质水平降低被认为是阿尔茨海默病进展的重要因素之一。 方法：在继续合成潜在的抗阿尔茨海默病药物和已知的含酰胺化合物的药理潜力的过程中，本研究介绍了两种新型酰胺基过渡金属锌 (II) 配合物 AAZ7 和 AAZ8 的合成，它们与杂环吡啶环相连，通过傅里叶变换红外光谱(FT-IR)、元素分析、1 H_NMR和13 C_NMR对其进行合成和表征。FT-IR 光谱记录显示，与游离配体相比，两种配合物中的 Δν 值都降低了，形成了二齿配体。分析了两种合成的复合物的乙酰胆碱酯酶和丁酰胆碱酯酶抑制潜力以及抗氧化活性。 结果：重要的是，与标准阳性对照加兰他敏相比，AAZ8 复合物表现出更强的活性，作为 AChE
• Synthesis, physicochemical characterizations and in vitro biological evaluations of amide based Zn(II) carboxylates
  作者：Muhammad Zubair、Muhammad Sirajuddin、Ali Haider、Kaleem Ullah、Irfan Ullah、Akhtar Munir、Saqib Ali、Muhammad Nawaz Tahir

  DOI：10.1016/j.ica.2018.07.005

  日期：2018.10

  Carboxylate ligands are widely used in chemistry and pharmacy owing to their ability to form stable complexes with a large variety of metal ions. In that context, carboxylate complexes allow modulation of the pharmaceutical products. Herein, a series of six novel Zn(II) carboxylates: [Zn(L-1)(2)] (1), [Zn(L-1)(2) (bipy)] (2), [Zn(L-1)(2) (phen)] (3), [Zn(L-2)(2)] (4), [Zn(L-2)(2) (bipy)] (5) and [Zn(L-2)(2) (phen)] (6) (where L-1 = 4-(2-methoxy-5-nitrophenylamino)-4-oxobutanoic acid), L-2 = 4-(2-nitro-4-methoxyphenylamino)-4-oxobutanoic acid), phen = 1,10-phenanthroline and bipy = 2,2'-bipyridine) were synthesized in good yield and successfully characterized by H-1, C-13 NMR, FT-IR and single-crystal X-ray crystallography. The spectroscopic data reveal that the absence of OH peak in the spectra of complexes confirm their formation. Single-crystal X-ray crystallographic data for complexes 1 and 5 show a distorted octahedral environment around the Zn atom. The results of both FTIR and single-crystal X-ray crystallography confirm the bidentate nature of the carboxylate ligands. The DNA interaction study of the synthesized complexes was investigated using UV-visible spectroscopy and viscosity measurements suggesting an intercalative binding mode of interaction of the complexes with SS-DNA. The interaction between the synthesized complexes and CTAB was elaborately studied with a conductometric method. The conductivity method was used to find CMC, higher CMC values suggesting a stable complex-CTAB system. Results of in vitro antibacterial and antifungal activities indicate the biological potency of the synthesized compounds.
• BALASUBRAMANIYAN, V.;BHATIA, V. G.;WAGH, S. B., TETRAHEDRON, 1983, 39, N 9, 1475-1485
  作者：BALASUBRAMANIYAN, V.、BHATIA, V. G.、WAGH, S. B.

  DOI：——

  日期：——