(E)-3-(3,4-dihydroxy-5-nitrophenyl)acrylic acid

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: (E)-3-(3,4-dihydroxy-5-nitrophenyl)acrylic acid
• 英文别名: 3-(3,4-Dihydroxy-5-nitrophenyl)prop-2-enoic acid；(E)-3-(3,4-dihydroxy-5-nitrophenyl)prop-2-enoic acid
• 化学式: C₉H₇NO₆
• 分子量: 225.158
• InChiKey: WIGNVYQMAXKHTQ-OWOJBTEDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  124
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  异丙醚 、 (E)-3-(3,4-dihydroxy-5-nitrophenyl)acrylic acid 以 甲醇 为溶剂， 生成 methyl 3,4-dihydroxy-5-nitrocinnamate
  参考文献：
  名称：

  Catechol derivatives

  摘要：

  公式##STR1##中的儿茶酚衍生物，其中Ra、Rb和Rc具有本文中给出的含义，以及在生理条件下可水解的酯和醚衍生物及其药学上可接受的盐已被描述，并具有有价值的药理特性。特别是，它们抑制儿茶酚-O-甲基转移酶(COMT)这种可溶性、依赖镁的酶，该酶催化S-腺苷甲硫氨酸的甲基基团转移到儿茶酚底物上，从而形成相应的甲基醚。可被COMT进行O-甲基化并因此被失活的适当底物包括，例如，外源性儿茶酚胺和具有儿茶酚结构的外源性给药的治疗活性物质。上述公式Ia不仅包括发明的一部分化合物，还包括已知的化合物；构成发明一部分的化合物可以按照已知方法制备。

  公开号：

  US05236952A1
• 作为产物：
  描述：

  5-nitroferulic acid 在 三溴化硼 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 1.0h， 生成 (E)-3-(3,4-dihydroxy-5-nitrophenyl)acrylic acid
  参考文献：
  名称：

  Synthesis and physico-chemical properties of nitrocaffeic acids

  摘要：

  The synthesis and spectroscopic properties of the three isomers of nitrocaffeic acid are described. The three pK(a) s of each isomer were measured by UV-visible spectroscopy. The comparison of the UV-visible spectra of nitrocaffeic acids and those obtained from the reaction of caffeic acid with reactive nitrogen species led to the conclusion that the nitration of caffeic acid with acidic nitrite does not significantly occur and confirmed the absence of nitration when caffeic acid reacts with peroxynitrite. Attempts to obtain free radical species from nitrocaffeic acids by classical methods showed a different reactivity to that of nitroaromatics and catechols. Nitrocaffeic acids do not autoxidize under aqueous basic conditions and are insensitive to t-BuOK or O-2(-.) (two reactants known for their capabilities to oxidize catechols and reduce nitroaromatics). Nitroaromatic anion radicals may be obtained using sodium borohydride as reductant and are particularly stable under an uncontrolled atmosphere. Copyright (C) 2000 John Wiley & Sons, Ltd.

  DOI：

  10.1002/1099-1395(200009)13:9<511::aid-poc283>3.0.co;2-8

文献信息

• Development of Blood–Brain Barrier Permeable Nitrocatechol-Based Catechol <i>O</i>-Methyltransferase Inhibitors with Reduced Potential for Hepatotoxicity
  作者：Tiago Silva、Tarek Mohamed、Arash Shakeri、Praveen P. N. Rao、Loreto Martínez-González、Daniel I. Pérez、Ana Martínez、Maria João Valente、Jorge Garrido、Eugenio Uriarte、Paula Serrão、Patrício Soares-da-Silva、Fernando Remião、Fernanda Borges

  DOI：10.1021/acs.jmedchem.6b00666

  日期：2016.8.25

  on the development of centrally active COMT inhibitors, which can be valuable assets for neurological disorders such as Parkinson’s disease, due to the severe hepatotoxicity risk associated with tolcapone. New nitrocatechol COMT inhibitors based on naturally occurring caffeic acid and caffeic acid phenethyl ester were developed. All nitrocatechol derivatives displayed potent inhibition of peripheral

  最近的努力集中在开发集中活性的COMT抑制剂上，由于与托卡朋有关的严重的肝毒性危险，它可以成为神经系统疾病（如帕金森氏病）的宝贵资产。开发了基于自然存在的咖啡酸和咖啡酸苯乙酯的新型硝基邻苯二酚COMT抑制剂。所有硝基儿茶酚衍生物在纳摩尔范围内均显示出对外周和大脑COMT的有效抑制。药物样衍生物13，15，和16预计在体外以50μM与大鼠原代肝细胞一起孵育时，它们会跨过血脑屏障，并且毒性显着低于tolcapone和entacapone。而且，它们独特的酸度和电化学性质降低了反应性醌-亚胺形成的机会，并因此降低了肝毒性的可能性。16的结合模式证实了与COMT的主要相互作用是通过硝基邻苯二酚环建立的，从而允许侧链衍生化以用于未来的铅优化工作。
• Catechol derivatives, their physiologically acceptable salts, esters and their use in the treatment of tissue damage induced by lipid peroxidation
  申请人：ORION-YHTYMÄ OY

  公开号：EP0444899A2

  公开（公告）日：1991-09-04

  Known and new catechol derivatives may be used as medicinal antioxidants in the prevention or treatment of tissue damage induced by lipid peroxidation. The conditions and diseases which may be treated are for example heart diseases, rheumatoid arthritis, cancer, inflammatory diseases, a rejection reaction in organ transplants, ischemia, cancer and aging.

  已知的和新的儿茶酚衍生物可用作药用抗氧化剂，用于预防或治疗脂质过氧化引起的组织损伤。可治疗的病症和疾病包括心脏病、风湿性关节炎、癌症、炎症性疾病、器官移植中的排异反应、缺血、癌症和衰老等。
• Synthesis of trans-caffeate analogues and their bioactivities against HIV-1 integrase and cancer cell lines
  作者：Chun-nian Xia、Hai-bo Li、Feng liu、Wei-xiao Hu

  DOI：10.1016/j.bmcl.2008.10.046

  日期：2008.12

  Forty caffeate analogues were synthesized via a convenient method starting from vanillin with moderate to good yields. The testing of biological activity of these compounds against HIV-1 integrase indicates that four compounds: bornyl caffeate, bornyl 2-nitrocaffeate, 5-nitrocaffeic acid and 5-nitrocaffeic acid phenethyl ester (5-nitroCAPE) possess a good HIV integrase inhibitory activity, IC50 19.9, 26.8, 25.0 and 13.5 mu M, respectively. Twelve caffeate analogues were tested by MTT assay on growth of human hepatocellular carcinoma BEL-7404, human breast MCF-7 adenocarcinoma, human lung A549 adenocarcinoma and human gastric cancer BCG823 cell lines, respectively. And the best result is IC50 5.5 mu M for CAPE against BEL-7404. (C) 2008 Elsevier Ltd. All rights reserved.
• Antioxidant properties of nitrocaffeic acids
  作者：Jean-Luc Grenier、Nicole Cotelle、Philippe Cotelle、Jean-Pierre Catteau

  DOI：10.1016/0960-894x(96)00048-0

  日期：1996.2

  A series of nitrodihydroxybenzenes and nitrocaffeic acids were prepared and their hydroxyl radical (OH degrees) and superoxide anion (O-2(-)) scavenging activities and xanthine oxidase inhibition activities were evaluated. 2-Nitrocaffeic acid is the more potent O-2(-) scavenger. 2-(and 5)-Nitrocaffeic acids are the more potent xanthine oxidase inhibitors.
• 3,5-Disubstituierte Pyrocatecholderivate
  申请人：F. HOFFMANN-LA ROCHE AG

  公开号：EP0237929B1

  公开（公告）日：1993-06-02