2-(2-carboxyethyl)-1,4-naphthoquinone

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-(2-carboxyethyl)-1,4-naphthoquinone
• 英文别名: 2-carboxyethyl-1,4-naphthoquinone；3-(1,4-dioxo-1,4-dihydronaphthalen-2-yl)propanoic acid；Naphthoquinonepropanoic acid；3-(1,4-dioxonaphthalen-2-yl)propanoic acid
• 化学式: C₁₃H₁₀O₄
• 分子量: 230.22
• InChiKey: SRGDDNIKFJKGLD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  71.4
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(2-carboxyethyl)-1,4-naphthoquinone 在 Fmoc-L-烯丙基甘氨酸 、 sodium chloride 、 iron(II) bromide 、 过氧化苯甲酰 作用下， 以 2-甲基-2-丁醇 为溶剂， 反应 6.0h， 以77%的产率得到
  参考文献：
  名称：

  一种铁催化醌类化合物氯化的方法

  摘要：

  本发明公开了一种铁催化醌类化合物氯化的方法，该方法包括如下步骤：在溶剂中，以氯化盐为氯试剂、过氧化物为氧化剂，铁为催化剂、氨基酸或其衍生物或新铜试剂为配体，氧化醌类化合物的烯键发生氯化反应生成氯取代的醌类化合物。本发明方法具有催化剂来源广泛、廉价和环保的优势；氧化剂来源广泛、廉价；氯化试剂温和、稳定和廉价；反应条件温和、选择性高和产率高；底物来源广泛且稳定；底物官能团相容性好且底物的适用范围广；天然产物也可以兼容，能很好的实现醌烯键上的氯化。在优化的反应条件之下，目标产品分离后产率可以高达90％。

  公开号：

  CN114426441A
• 作为产物：
  描述：

  methyl 3-(1,4-dioxo-1,4-dihydronaphthalen-2-yl)propionate 在 盐酸 、 水 作用下， 以42%的产率得到2-(2-carboxyethyl)-1,4-naphthoquinone
  参考文献：
  名称：

  TYPE 1, 4-NAPHTOQUINONE COMPOUNDS, COMPOSITIONS COMPRISING THEM AND USE OF THESE COMPOUNDS AS ANTI-CANCER AGENTS

  摘要：

  这项发明涉及以下给定的化合物（I）的公式或其药学上可接受的盐之一，作为药物；包含一个或多个具有公式（I）的化合物作为活性成分的药物组合物的公式（I），使用具有公式（I）的化合物制备旨在预防或治疗涉及异常细胞增殖的至少一种疾病的组合物，包含至少一种具有公式（I）的化合物的促凋亡组合物和/或抗增殖组合物，以及使用具有公式（I）的化合物作为促凋亡和/或抗增殖剂。

  公开号：

  US20090247472A1

文献信息

• Rational designed highly sensitive NQO1-activated near-infrared fluorescent probe combined with NQO1 substrates in vivo: An innovative strategy for NQO1-overexpressing cancer theranostics
  作者：Qijie Gong、Fulai Yang、Jiabao Hu、Tian Li、Pengfei Wang、Xiang Li、Xiaojin Zhang

  DOI：10.1016/j.ejmech.2021.113707

  日期：2021.11

  Since NQO1 is overexpressed in many cancer cells, it can be used as a biomarker for cancer diagnosis and targeted therapy. NQO1 substrates show potent anticancer activity through the redox cycle mediated by NQO1, while the NQO1 probes can monitor NQO1 levels in cancers. High sensitivity of probes is needed for diagnostic imaging in clinic. In this study, based on the analysis of NQO1 catalytic pocket

  由于 NQO1 在许多癌细胞中过表达，因此可用作癌症诊断和靶向治疗的生物标志物。NQO1 底物通过 NQO1 介导的氧化还原循环显示出有效的抗癌活性，而 NQO1 探针可以监测癌症中的 NQO1 水平。临床诊断成像需要高灵敏度的探针。本研究基于对 NQO1 催化口袋的分析，通过扩展苯醌触发基团10的芳香平面，合理设计了萘醌触发基团13。显示对 NQO1 的敏感性显着增加。基于萘醌触发基团的探针 A 在体内的灵敏度是基于苯醌触发基团的探针 B 的 8 倍。探针 A 对 NQO1 具有选择性和有效的敏感性，具有良好的安全性和血浆稳定性，使其首次在体内与 NQO1 底物结合用于过表达 NQO1 的癌症治疗。
• REVERSIBLY REDUCIBLE MATERIALS AND USE THEREOF
  申请人：University of Kentucky Research Foundation

  公开号：US20180099917A1

  公开（公告）日：2018-04-12

  Provided herein are a reversibly reducible material and a method of forming a reversibly reducible material. The reversibly reducible material includes the molecular formula: wherein each of R 1 , R 2 , R 3 , and R 4 are independently selected from the group consisting of hydrogen, oxygen, alkyl, cycloalkyl, O-alkyl, amine, quaternary ammonium, and sulfonate; R 5 is selected from the group consisting of hydrogen, halogen, alkyl, alkoxy, and amine; X is selected from the group consisting of hydrogen, branched or un-branched alkyl chain having 1-8 atoms containing 0-3 oxygen or nitrogen atoms, and substituted or unsubstituted aryl; and Z is selected from the group consisting of branched or un-branched alkyl chain having 1-8 atoms containing 0-3 oxygen or nitrogen atoms, and substituted or unsubstituted aryl. The method of forming a reversibly reducible material comprising reacting a quinone with an amine in an ethereal solvent. Also provided herein is a negolyte.

  本文提供了一种可逆还原材料和形成可逆还原材料的方法。 可逆还原材料包括分子式：其中R1、R2、R3和R4中的每一个独立地选择自氢、氧、烷基、环烷基、O-烷基、胺、季铵盐和磺酸的群; R5选择自氢、卤素、烷基、烷氧基和胺的群; X选择自氢、1-8个原子的具有0-3个氧或氮原子的分支或非分支烷基链，以及取代或未取代芳基; Z选择自1-8个原子的分支或非分支烷基链，包含0-3个氧或氮原子，以及取代或未取代芳基。 形成可逆还原材料的方法包括在醚溶剂中将喹醌与胺反应。 本文还提供了一种negolyte。
• Citterio, Attilio; Vismara, Elena; Bernardi, Rosanna, Journal of Chemical Research, Miniprint, 1983, # 4, p. 876 - 890
  作者：Citterio, Attilio、Vismara, Elena、Bernardi, Rosanna

  DOI：——

  日期：——
• Tailoring 1,4-naphthoquinone with electron-withdrawing group: toward developing redox polymer and FAD-GDH based hydrogel bioanode for efficient electrocatalytic glucose oxidation
  作者：Chuantao Hou、Qiaolin Lang、Aihua Liu

  DOI：10.1016/j.electacta.2016.06.078

  日期：2016.9

  Redox polymer hydrogels have been proved to be very promising for biofuel cells design and electrochemical biosensing. Here we report that a facile hydrogel bioanode based on electron-withdrawing nitro-group tailored 1,4-naphthoquinone (1,4-NQ)-appended redox polymer and flavin adenine dinucleotide-dependent glucose dehydrogenase (FAD-GDH) can dramatically improve the catalytic performance of glucose oxidation, for which a high current density of 1.97 + 0.06 mA cm(-2) and low onset potential of -0.13 V (vs. Ag/AgCl) can be achieved in 50 mM glucose solution without using any nanomaterials as electrode supports. Further, both electron-donating groups modified 1,4-NQs and electron-withdrawing nitro-group 1,4-NQs were synthesized to investigate their electrochemical properties. It was found that the enhanced catalytic performance can be mainly contributing from the nitro group-modified 1,4-NQs appended redox polymer, which shifted the formal potential in the positive direction and provided sufficient electrochemical driving force for glucose oxidation. Finally, this hydrogel bioanode was combined with a bilirubin oxidase based biocathode to construct a single-compartment glucose/O-2 biofuel cell with a high power output of 0.28 +/- 0.03 mW cm(-2) and open circuit potential of 0.69 V. Moreover, the O-2-insensitive FAD-GDH could improve the cell stability obviously compared with glucose oxidase based cell. This study provides an alternative route to develop glucose biosensor or biofuel cell for directly harvesting energy from glucose. (C) 2016 Elsevier Ltd. All rights reserved.
• EP1015422A4
  申请人：——

  公开号：EP1015422A4

  公开（公告）日：2004-12-08