(2-(2,6-二氯-4-羟基苯胺基)-5-羟基苯基)乙酸 | 69002-86-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: (2-(2,6-二氯-4-羟基苯胺基)-5-羟基苯基)乙酸
• 英文名称: 4',5-Dihydroxydiclofenac
• 英文别名: 2-[2-(2,6-dichloro-4-hydroxyanilino)-5-hydroxyphenyl]acetic acid
• CAS: 69002-86-4
• 化学式: C₁₄H₁₁Cl₂NO₄
• 分子量: 328.152
• InChiKey: DRZFITWJHHNHAD-UHFFFAOYSA-N

物化性质

• 熔点：
  217-219 °C
• 沸点：
  465.4±45.0 °C(Predicted)
• 密度：
  1.611±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  89.8
• 氢给体数：
  4
• 氢受体数：
  5

ADMET

代谢

4',5-二羟基双氯芬酸已知的人体代谢产物包括 (2S,3S,4S,5R)-6-[4-[2-(羧甲基)-4-羟基苯甲酰胺]-3,5-二氯苯氧基]-3,4,5-三羟基氧杂环己烷-2-羧酸和 2-[2-(2,6-二氯-4-磺酸氧基苯甲酰胺)-5-羟基苯基]乙酸。

4',5-Dihydroxydiclofenac has known human metabolites that include (2S,3S,4S,5R)-6-[4-[2-(carboxymethyl)-4-hydroxyanilino]-3,5-dichlorophenoxy]-3,4,5-trihydroxyoxane-2-carboxylic acid and 2-[2-(2,6-dichloro-4-sulfooxyanilino)-5-hydroxyphenyl]acetic acid.

来源:NORMAN Suspect List Exchange

反应信息

• 作为产物：
  描述：

  N-acetyl-N-(4-methoxyphenyl)-2,6-dichloro-4-methoxyaniline 在 氢碘酸 氢氧化钾 、 sodium hydroxide 、 草酸氯化物 作用下， 生成 (2-(2,6-二氯-4-羟基苯胺基)-5-羟基苯基)乙酸
  参考文献：
  名称：

  双氯芬酸的肝代谢：人CYP在次要氧化途径中的作用

  摘要：

  这项研究的目的是重新检查双氯芬酸的人肝代谢，特别关注与药物特异肝毒性有关的次要羟基化代谢产物的产生。使用了不同的实验方法：人肝细胞，人微粒体和表达单个人CYP（细胞色素P450）的工程细胞。人肝细胞形成了3'-羟基-，4'-羟基-，5-羟基-4'，5-二羟基和N，5-二羟基双氯芬酸，以及几种内酰胺。人肝微粒体形成4'-和5-羟基双氯芬酸的过程遵循Michaelis-Menten动力学（Km 9 +/- 1 microM; Vmax 432 +/- 15 pmol / min / mg和Km 43 +/- 5 microM;和Vmax分别为15.4 +/- 0.6 pmol / min / mg）。将5-羟基双氯芬酸与人肝微粒体温育后检测到次生代谢物，产生4'，5-二羟基双氯芬酸（Km 15 +/- 1 microM; Vmax 96 +/- 3 pmol / min / mg）和少量的N，

  DOI：

  10.1016/s0006-2952(99)00167-7

文献信息

• Biobased Poly(ethylene furanoate) Polyester/TiO2 Supported Nanocomposites as Effective Photocatalysts for Anti-inflammatory/Analgesic Drugs
  作者：Anastasia Koltsakidou、Zoi Terzopoulou、George Kyzas、Dimitrios Bikiaris、Dimitra Lambropoulou

  DOI：10.3390/molecules24030564

  日期：——

  In the present study, polymer supported nanocomposites, consisting of bio-based poly(ethylene furanoate) polyester and TiO2 nanoparticles, were prepared and evaluated as effective photocatalysts for anti-inflammatory/analgesic drug removal. Nanocomposites were prepared by the solvent evaporation method containing 5, 10, 15, and 20 wt% TiO2 and characterized using Fourier Transform Infrared spectroscopy (FTIR), differential scanning calorimetry (DSC), wide-angle X-ray diffraction (WAXD), thermogravimetric analysis (TGA), and scanning electron microscopy (SEM). Thin films of them have been prepared by the melt press and optimization of the photocatalytic procedure was conducted for the most efficient synthesized photocatalyst. Finally, mineralization was evaluated by means of Total organic carbon (TOC) reduction and ion release, while the transformation products (TPs) generated during the photocatalytic procedure were identified by high-resolution mass spectrometry.

  在本研究中，制备并评估了由生物基聚乙烯呋喃酮聚酯和二氧化钛纳米颗粒组成的聚合物支撑纳米复合材料，作为抗炎/镇痛药物去除的有效光催化剂。纳米复合材料通过溶剂蒸发法制备，含有5、10、15和20 wt%的二氧化钛，并利用傅里叶变换红外光谱（FTIR）、差示扫描量热法（DSC）、宽角X射线衍射（WAXD）、热重分析（TGA）和扫描电子显微镜（SEM）进行表征。通过熔融压制制备了它们的薄膜，并对最有效的合成光催化剂进行了光催化程序的优化。最后，通过总有机碳（TOC）减少和离子释放评估了矿化，同时通过高分辨质谱鉴定了光催化程序中生成的转化产物（TPs）。
• Degradation kinetics and mechanism of diclofenac by UV/peracetic acid
  作者：Li Zhang、Yiqing Liu、Yongsheng Fu

  DOI：10.1039/d0ra00363h

  日期：——

  In this work, the degradation kinetics and mechanism of diclofenac (DCF) by UV/peracetic acid (PAA) was investigated. The effects of pH, PAA dose and common water components such as inorganic ions and dissolved organic matter (DOM) on DCF degradation by UV/PAA were also evaluated. It was observed that the addition of PAA promoted the photodegradation of DCF due to the generation of reactive radicals

  在这项工作中，研究了紫外/过氧乙酸 (PAA) 对双氯芬酸 (DCF) 的降解动力学和机理。还评估了 pH 值、PAA 剂量和常见水成分（如无机离子和溶解有机物 (DOM)）对 UV/PAA 降解 DCF 的影响。观察到 PAA 的加入促进了 DCF 的光降解，原因是 PAA 光解过程中产生了反应性自由基，自由基清除实验也证实了这一点。DCF 的最佳降解效率在 pH 8.5 时获得。随着 PAA 剂量的增加，DCF 的去除逐渐增强。由于NO 3 -是一种光敏物质，在紫外光照射下会产生HO˙，它的存在促进了DCF的降解。CO 3 2−的存在可以稍微改善 DCF 的降解，这可能是由于生成的碳酸盐自由基的作用。Cl -、SO 4 2-和Fe 3+对DCF去除的影响不大，而Cu 2+由于其对PAA分解的催化能力，可以促进DCF的降解。DOM存在对DCF去除有抑制作用，DOM浓度越高越明显。总有机碳
• Electrochemical oxidation of diclofenac on CNT and M/CNT modified electrodes
  作者：M. Ferreira、S. Güney、I. Kuźniarska-Biernacka、O. S. G. P. Soares、J. L. Figueiredo、M. F. R. Pereira、I. C. Neves、A. M. Fonseca、P. Parpot

  DOI：10.1039/d1nj01117k

  日期：——

  calculated from the scan rate study. Cyclic voltammograms show several oxidation processes, which confirm the interaction between DCF and the catalyst surface necessary for direct oxidation processes. Constant potential electrolysis of DCF was carried out on carbon nanotubes (CNT) and metal supported CNT (M/CNT) modified electrodes, in 0.1 M NaOH and 0.1 M Na2CO3/NaHCO3 buffer media. The highest DCF conversion

  双氯芬酸 (DCF) 是一种被认为是一种新兴污染物（经常在废水中检测到）的非甾体抗炎药，在水性介质中基于碳东丽的 CNT、Pt/CNT 和 Ru/CNT 改性电极进行了电化学氧化研究. 使用循环伏安法研究 DCF 在这些修饰电极上的电反应性，并从扫描速率研究计算动力学参数。循环伏安图显示了几个氧化过程，这证实了 DCF 与直接氧化过程所需的催化剂表面之间的相互作用。在碳纳米管 (CNT) 和金属负载的 CNT (M/CNT) 修饰电极上，在 0.1 M NaOH 和 0.1 M Na 2 CO 3 /NaHCO 3 中进行 DCF 的恒电位电解缓冲介质。在碳酸盐缓冲介质中发现了最高的 DCF 转化率（电解 8 小时后为 88%），对于 Ru/CNT，而在 Pt/CNT 修饰电极上获得了最佳的碳矿化效率（对应于氧化 DCF 的 48%）。 0.1 M NaOH 培养基。电解产物通过 HPLC
• Albumin-binding compounds that prevent nonenzymatic glycation and that may be used for treatment of glycation-related pathologies
  申请人：——

  公开号：US20010034359A1

  公开（公告）日：2001-10-25

  The present invention is directed to compositions that inhibit the nonenzymatic glycation of albumin, as well as methods of using compounds that inhibit albumin glycation for the treatment of glycation-related pathologies.

  本发明涉及抑制白蛋白非酶促糖基化的组合物，并使用抑制白蛋白糖基化的化合物治疗糖基化相关病理的方法。
• Synthesis and quantitative structure-activity relationships of diclofenac analogs
  作者：Peter Moser、Alfred Sallmann、Irmgard Wiesenberg

  DOI：10.1021/jm00171a008

  日期：1990.9

  The synthesis of a series of 2-anilinophenylacetic acids, close analogues of diclofenac, is described. These compounds were tested in two models used for evaluating the activity of nonsteroidal antiinflammatory drugs (NSAID's), inhibition of cyclooxygenase enzyme activity in vitro, and adjuvant-induced arthritis (AdA) in rats. Statistically significant correlations were found between the inhibitory activities of the compounds in these two models, indicating that cyclooxygenase inhibition seems to be the underlying mechanism for the antiinflammatory activity of these compounds. Quantitative structure-activity relationship (QSAR) analysis revealed that the crucial parameters for activity in both models were the lipophilicity and the angle of twist between the two phenyl rings. Optimal activities were associated with halogen or alkyl substituents in both ortho positions of the anilino ring. Compounds with OH groups in addition to two ortho substituents or compounds with only one or no ortho substituents were less active.