5-硝基-2-糠乙酯 | 943-37-3

• 物质功能分类: 化学试剂 - 有机试剂 - 酯类
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 呋喃
• 中文名称: 5-硝基-2-糠乙酯
• 中文别名: 5-硝基-2-糖酸乙酯
• 英文名称: 5-nitrofuran-2-carboxylic acid ethyl ester
• 英文别名: ethyl 5-nitrofuran-2-carboxylate；Ethyl 5-nitro-2-furoate
• CAS: 943-37-3
• 化学式: C₇H₇NO₅
• mdl: MFCD00092566
• 分子量: 185.136
• InChiKey: JMNXLAQKIHVFIC-UHFFFAOYSA-N

物化性质

• 熔点：
  98-101°C

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.285
• 拓扑面积：
  85.3
• 氢给体数：
  0
• 氢受体数：
  5

安全信息

• 安全说明：
  S22,S24/25
• RTECS号：
  LV2012500
• 海关编码：
  2932190090
• 储存条件：
  室温

反应信息

• 作为反应物：
  描述：

  5-硝基-2-糠乙酯 在 钯 作用下， 以 乙醇 为溶剂， 生成 ethyl 2-amino-furan-5-carboxylate
  参考文献：
  名称：

  Hypolipidemic and antiatherosclerotic novel

  摘要：

  这份披露描述了一种新型（单取代氨基）杂环芳基羧酸及其类似物，可用作降脂和抗动脉粥样硬化药物。

  公开号：

  US04382143A1
• 作为产物：
  描述：

  5-硝基-2-糠酸 在 对甲苯磺酸 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 生成 5-硝基-2-糠乙酯
  参考文献：
  名称：

  Hypolipidemic and antiatherosclerotic novel

  摘要：

  这份披露描述了一种新型（单取代氨基）杂环芳基羧酸及其类似物，可用作降脂和抗动脉粥样硬化药物。

  公开号：

  US04382143A1

文献信息

• [EN] QUINOLONE ANTIBACTERIAL AGENTS<br/>[FR] AGENTS ANTIBACTERIENS A BASE DE QUINOLONE
  申请人：WARNER LAMBERT CO

  公开号：WO2005026165A1

  公开（公告）日：2005-03-24

  Compounds of formula I and methods for their preparation are disclosed. Further disclosed are methods of making biologically active compounds of formula I as well as pharmaceutically acceptable compositions comprising compounds of formula I. Compounds of formula I as disclosed herein can be used in a variety of applications including use as antibacterial agents.

  公开了式I的化合物及其制备方法。进一步公开了制备式I生物活性化合物的方法，以及包括式I化合物的药用可接受组合物。本文公开的式I化合物可用于各种应用，包括用作抗菌剂。
• AMINOPYRAZOLE DERIVATIVES
  申请人：Bur Daniel

  公开号：US20110034516A1

  公开（公告）日：2011-02-10

  The invention relates to aminopyrazole derivatives of formula (I), wherein A, E, R 1 and R 2 are as defined in the description, their preparation and their use as pharmaceutically active compounds.

  这项发明涉及公式（I）的氨基吡唑衍生物， 其中A、E、R1和R2如描述中所定义，它们的制备以及它们作为药用活性化合物的用途。
• Synthesis, &lt;i&gt;in Vitro&lt;/i&gt; and &lt;i&gt;in Silico&lt;/i&gt; Studies of Some Novel 5-Nitrofuran-2-yl Hydrazones as Antimicrobial and Antitubercular Agents
  作者：Hatem Abdel-Kader Abdel-Aziz、Wagdy Mohamed Eldehna、Mohamed Fares、Tilal Elsaman、Marwa Mostafa Abdel-Aziz、Dalia Hussein Soliman

  DOI：10.1248/bpb.b15-00439

  日期：——

  In this study, we synthesized two series of novel 5-nitrofuran-2-carbohydrazides 21a–h and 22a–e in addition to a third series of thiophene-2-carbohydrazides 23a–g to develop potent antimicrobial and/or antitubercular agents. The newly synthesized compounds were evaluated in vitro for their antimicrobial and antimycobacterial activities. Most of the 5-nitrofuran-2-carbohydrazides 21a–h and 22a–e displayed variable activity against Aspergillus fumigates, Staphylococcus aureus, Streptococcus pneumonia, Bacillis subtilis, Salmonella typhimurium, Klebsiella pneumonia, Escherichia coli and Mycobacterium tuberculosis. The sulfonamide derivative 21f exhibited superior potency and broad-spectrum antimicrobial activity with minimum inhibitory concentration (MIC)=0.06–0.98 µg/mL and antimycobacterial activity with MIC=3.9 µg/mL. The 5-nitrofuran-2-carbohydrazides 21a, b, g, h and 22a–c exhibited significant antibacterial activity with MIC values in the range of 0.12–7.81 µg/mL. The significances of the 5-nitrofuran moiety and sulfonamide function were explored via the structure–activity relationship (SAR) study. In addition, docking studies revealed that the p-amino benzoic acid (PABA) and binding pockets of the dihydropteroate synthase (DHPS) were successfully occupied by compound 21f. Furthermore, two quantitative structure–activity relationship (QSAR) models were built to explore the structural requirements which controlled the activity.

  在本研究中，我们合成了两系列新型5-硝基呋喃-2-甲酰肼21a–h和22a–e，以及第三系列噻吩-2-甲酰肼23a–g，旨在开发强效抗菌和/或抗结核剂。新合成的化合物在体外进行了抗菌和抗分枝杆菌活性评估。大多数5-硝基呋喃-2-甲酰肼21a–h和22a–e对烟曲霉、金黄色葡萄球菌、肺炎链球菌、枯草芽孢杆菌、鼠伤寒沙门氏菌、肺炎克雷伯菌、大肠埃希菌和结核分枝杆菌显示出不同程度的活性。磺胺衍生物21f表现出优越的广谱抗菌活性，最小抑制浓度（MIC）=0.06–0.98 µg/mL，以及抗分枝杆菌活性，MIC=3.9 µg/mL。5-硝基呋喃-2-甲酰肼21a、b、g、h和22a–c显示出显著的抗菌活性，MIC值在0.12–7.81 µg/mL范围内。通过结构-活性关系（SAR）研究探讨了5-硝基呋喃部分和磺胺功能的重要性。此外，对接研究揭示了化合物21f成功占据了对氨基苯甲酸（PABA）和二氢蝶酸合酶（DHPS）的结合口袋。进一步地，构建了两个定量结构-活性关系（QSAR）模型，以探索控制活性的结构要求。
• Synthesis and Structural Pattern Recognition of 5-(2'-Alkoxycarbonyl-substituted phenoxy)furfural Derivatives
  作者：Chia-Lin Chang

  DOI：10.1248/cpb.57.550

  日期：——

  The ethyl 5-(2′-alkoxycarbonyl-substituted phenoxy)furan-2-carboxylates (1C—13C) showed good anti-platelet aggregation,1) anti-allergic2) and anti-inflammatory activities.2) A series of 5-(2′-alkoxycarbonyl-substituted phenoxy)furfurals (1F—13F) were prepared for comparing the above activities. The objectives of this research are the synthesis and structural pattern recognition of compounds 1F—13F. The Silica Gel 60 column chromatography method was employed to separate and purify pure compounds 1F—13F by three solvent systems. For the structure elucidation of compounds 1F—13F, four spectroscopic methods were used: electron impact mass (EI-MS), UV–VIS, IR and NMR spectrometers. With the help of spectrometers, investigations can be performed on spectroscopic data. A simple methodology for recognizing structural patterns was carried out with the aid of statistical analysis designed to establish the classification model of the structural skeleton in this research. It was found that compounds 1C—13C and 1F—13F have similar chemical profiles and are clustered into one group. The pattern plots revealed valuable information and showed good correlation between compounds 1C—13C and 1F—13F. These findings correlate directly with the resulting spectroscopic data. These results with those obtained by EI-MS and NMR patterns give insight into a reliable pattern recognition for determining both 1C—13C and 1F—13F skeletons.

  乙基5-(2′-烷氧羰基取代苯氧基)呋喃-2-羧酸酯(1C—13C)显示出良好的抗血小板聚集、1)抗过敏2)和抗炎活性。2)制备了一系列5-(2′-烷氧羰基取代苯氧基)糠醛(1F—13F)以比较上述活性。本研究的目标是合成化合物1F—13F并进行结构模式识别。采用硅胶60柱色谱法通过三种溶剂系统分离纯化纯化合物1F—13F。为了阐明化合物1F—13F的结构，使用了四种光谱方法：电子轰击质谱(EI-MS)、UV-VIS、IR和NMR光谱仪。在光谱仪的帮助下，可以对光谱数据进行研究。通过统计分析设计了一种简单的结构模式识别方法，旨在建立本研究中结构骨架的分类模型。发现化合物1C—13C和1F—13F具有相似的化学特征，并被归为一组。模式图揭示了有价值的信息，并显示了化合物1C—13C和1F—13F之间的良好相关性。这些发现与光谱学数据的结果直接相关。这些结果以及通过EI-MS和NMR模式获得的结果，为确定1C—13C和1F—13F骨架的可靠模式识别提供了见解。
• Synthesis of phenyl furyl sulfides and phenyl furyl ethers by nucleophilic substitution of nitrofurans
  作者：Masayuki Ogawa、Katsuya Sakuma、Hiroshi Okamoto、Jyunichi Koyanagi、Kouji Nakayama、Akira Tanaka、Katsumi Yamamoto

  DOI：10.1002/jhet.5570440527

  日期：2007.9

  Phenyl furyl sulfides (3a-j) and phenyl furyl ethers (3k-n), which are useful in synthesizing furocondensed 3-ring compounds, can be synthesized by nucleophilic substitution of nitrofurans having electron withdrawal groups. In our experiments using 5-nitrofurans having electron withdrawal groups (2a-i), nucleophilic substitution readily occurred with the benzenethiolate anion of thiosalicylic acid

  可以通过亲核取代具有电子撤离基团的硝基呋喃来合成用于合成呋喃缩合的3-环化合物的苯基呋喃基硫化物（3a-j）和苯基呋喃基醚（3k-n）。在我们使用具有电子撤离基团（2a-i）的5-硝基呋喃的实验中，亲核取代容易发生在硫代水杨酸的苯硫醇根阴离子（1a），硫代水杨酸酯的苯硫醇根阴离子（1b）和水杨酸酯的苯甲酸根阴离子（1c-d）得到苯基呋喃基硫醚（3a-j）和苯基呋喃基醚（3k-n）。