2,5-dihydroxy-3,6-bis-(4-methoxy-phenyl)-[1,4]benzoquinone | 38558-72-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 2,5-dihydroxy-3,6-bis-(4-methoxy-phenyl)-[1,4]benzoquinone
• 英文别名: 2,5-Dihydroxy-3,6-bis-(4-methoxy-phenyl)-[1,4]benzochinon；2,5-Dihydroxy-3,6-bis(4-methoxyphenyl)-2,5-cyclohexadiene-1,4-dione；2,5-dihydroxy-3,6-bis(4-methoxyphenyl)cyclohexa-2,5-diene-1,4-dione
• CAS: 38558-72-4
• 化学式: C₂₀H₁₆O₆
• 分子量: 352.343
• InChiKey: DOTVVGIJKMIBHU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  26
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  93.1
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2,5-dihydroxy-3,6-bis-(4-methoxy-phenyl)-[1,4]benzoquinone 在 盐酸 、 氢氧化钾 、 硫酸 作用下， 以 1,4-二氧六环 为溶剂， 反应 4.0h， 生成 rickenyl E
  参考文献：
  名称：

  Butlerins D, E and F-Three New Hexasubstituted Lichen p-Terphenyls

  摘要：

  Butlerin D（4）（3'，4，4"，5'，6'-五甲氧基[1,1':4',1"-二苯基]-2'-乙酸酯），butlerin E（5）（3'，4，4'6'-四甲氧基[1,1':4',1"-二苯基]-2',5'-二乙酸酯）和butlerin F（6）（3'，4，4"，5'-四甲氧基[1,1":4',1"-二苯基]-2',6'-二乙酸酯）已被合成，并显示与地衣Relicina connivens中的usnic酸、butlerin A（1）、butlerin B（2）和butlerin C（3）共存。

  DOI：

  10.1071/ch9961247
• 作为产物：
  描述：

  4'-甲氧基乙酰苯胺 在 氢氧化钾 、 乙醇 、 dinitrogen tetraoxide 作用下， 生成 2,5-dihydroxy-3,6-bis-(4-methoxy-phenyl)-[1,4]benzoquinone
  参考文献：
  名称：

  528.羟基多酚酸和相关化合物作为亚油酸和亚油酸甲酯的抗氧化剂

  摘要：

  DOI：

  10.1039/jr9620002753

文献信息

• Discovery of a novel inhibitor of NAD(P)+-dependent malic enzyme (ME2) by high-throughput screening
  作者：Yi Wen、Lei Xu、Fang-lei Chen、Jing Gao、Jing-ya Li、Li-hong Hu、Jia Li

  DOI：10.1038/aps.2013.189

  日期：2014.5

  Malic enzymes are oxidative decarboxylases with NAD+ or NAD(P)+ as cofactor that catalyze the conversion of L-malate to pyruvate and CO2. The aim of this study was to discover and characterize a potent inhibitor of human NAD(P)+-dependent malic enzyme 2 (ME2). Recombinant human ME2-His-Tag fusion protein was overexpressed in E coli and purified with Ni-NTA resin. A high-throughput screening (HTS) assay was developed to find ME2 inhibitors. Detergent Brij-35 was used to exclude false positives. The characteristics of the inhibitor were analyzed with enzyme kinetics analysis. A thermal shift assay for ME2 was carried out to verify the binding of the inhibitor with the enzyme. An HTS system for discovering ME2 inhibitors was established with a Z′ factor value of 0.775 and a signal-to-noise ratio (S/N) of 9.80. A library containing 12 683 natural products was screened. From 47 hits, NPD387 was identified as an inhibitor of ME2. The primary structure-activity relationship study on NPD387 derivatives showed that one derivative NPD389 was more potent than the parent compound NPD387 (the IC50 of NPD389 was 4.63±0.36 μmol/L or 5.59±0.38 μmol/L, respectively, in the absence or presence of 0.01% Brij-35 in the assay system). The enzyme kinetics analysis showed that NPD389 was a fast-binding uncompetitive inhibitor with respect to the substrate NAD+ and a mixed-type inhibitor with respect to the substrate L-malate. NPD389 is a potent ME2 inhibitor that binds to the enzyme in a fast-binding mode, acting as an uncompetitive inhibitor with respect to the substrate NAD+ and a mixed-type inhibitor with respect to the substrate L-malate.

  苹果酸酶是以NAD+或NAD(P)+为辅助因子的氧化脱羧酶，催化L-苹果酸转化为丙酮酸和二氧化碳。本研究的目的是发现并表征人类NAD(P)+依赖的苹果酸酶2（ME2）的有效抑制剂。重组人ME2-His-Tag融合蛋白在大肠杆菌中过表达，并用Ni-NTA树脂纯化。开发了高通量筛选（HTS）分析以寻找ME2抑制剂。使用洗涤剂Brij-35以排除假阳性。通过酶动力学分析分析了抑制剂的特性。对ME2进行了热转变实验，以验证抑制剂与酶的结合。建立了发现ME2抑制剂的HTS系统，Z'因子值为0.775，信噪比（S/N）为9.80。筛选了包含12683种天然产物的文库。最终，从47个命中中识别出NPD387作为ME2的抑制剂。对NPD387衍生物的初步结构-活性关系研究显示，衍生物NPD389的效能优于母化合物NPD387（NPD389在无0.01% Brij-35和有0.01% Brij-35的实验体系中的IC50分别为4.63±0.36 μmol/L和5.59±0.38 μmol/L）。酶动力学分析显示NPD389对于底物NAD+是一种快速结合的非竞争抑制剂，对于底物L-苹果酸则是一种混合型抑制剂。NPD389是一种有效的ME2抑制剂，以快速结合的方式与酶结合，作为对底物NAD+的非竞争抑制剂和对底物L-苹果酸的混合型抑制剂。
• Comparative analysis of p-terphenylquinone and seriniquinone derivatives as reactive oxygen species-modulating agents
  作者：Haruna Nagao、Masayuki Ninomiya、Hodaka Sugiyama、Atsuya Itabashi、Kaho Uno、Kaori Tanaka、Mamoru Koketsu

  DOI：10.1016/j.bmcl.2022.128992

  日期：2022.11

  Quinones are widespread in plants, animals, insects, and microorganisms. Several anticancer agents contain quinone structures as critical parts to show remarkable potential and distinctive modes of actions. The purpose of this study was to investigate the structure–activity relationships of microbial quinones and their derivatives as anticancer agents. A series of p-terphenylquinone and seriniquinone

  醌广泛存在于植物、动物、昆虫和微生物中。几种抗癌剂含有醌结构作为关键部分，显示出显着的潜力和独特的作用模式。本研究的目的是研究微生物醌及其衍生物作为抗癌剂的结构-活性关系。由此制备了一系列对三联苯醌和丝氨酸醌衍生物。合成醌的处理对人白血病 HL-60 细胞具有剂量依赖性的抗增殖活性。此外，丝氨酸醌衍生物会升高细胞活性氧（ROS）水平，从而引发随后的细胞凋亡事件。我们的研究结果强调了丝氨酸醌衍生物作为氧化还原循环诱导的 ROS 调节抗癌剂的巨大潜力。
• Bioinspired Synthesis of Pulvinic Acids Including Xerocomic Acid and Fluorescence Properties of Bis‐lactone Intermediates
  作者：Élodie Pradayrol、Blandine Séon‐Méniel、Samuel Oger、Biraveena Sinniah‐Kandiah、Régis Guillot、Rémi Franco、Martin Souce、Athéna Kasselouri、Alexandre Maciuk、Laurent Evanno

  DOI：10.1002/ejoc.202201152

  日期：2023.2.17

  Six pulvinic acids (pulvinic, pinastric, atromentic, xerocomic, isoxerocomic, variegatic) and a polyporic acid (atromentin) were synthesised. A set of terphenyl-quinones was prepared through sequential Suzuki-Miyaura couplings. Then, a rearrangement into pulvinic bis-lactones was induced by the action of Ac2O/DMSO. Ring openings and deprotections achieved total syntheses. Fluorescence properties of

  合成了六种 pulvinic acids (pulvinic, pinastric, atromentic, xerocomic, isoxerocomic, variegatic) 和多孔酸 (atromentin)。通过连续的 Suzuki-Miyaura 偶联制备了一组三联苯醌。然后，通过 Ac 2 O/DMSO的作用诱导重排为 pulvinic 双内酯。开环和脱保护实现了全合成。确定了双内酯的荧光特性。
• Koegl; Becker, Justus Liebigs Annalen der Chemie, 1928, vol. 465, p. 212,232
  作者：Koegl、Becker

  DOI：——

  日期：——
• Koegl, Justus Liebigs Annalen der Chemie, 1928, vol. 465, p. 253
  作者：Koegl

  DOI：——

  日期：——