5,7,3',4',5'-五羟基黄酮 | 520-31-0

• 物质功能分类: 有机原料 - 酮类化合物
• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 黄酮类化合物
• 中文名称: 5,7,3',4',5'-五羟基黄酮
• 英文名称: tricetin
• 英文别名: 5,7,3',4',5'-pentahydroxyflavone；myricetin；5,7,3',4',5'-Pentahydroxyflavon；hieracin；5,7-dihydroxy-2-(3,4,5-trihydroxyphenyl)chromen-4-one
• CAS: 520-31-0
• 化学式: C₁₅H₁₀O₇
• 分子量: 302.24
• InChiKey: ARSRJFRKVXALTF-UHFFFAOYSA-N

物化性质

• 熔点：
  >330 °C (decomp)
• 沸点：
  721.7±60.0 °C(Predicted)
• 密度：
  1.763±0.06 g/cm3(Predicted)
• 溶解度：
  可溶于DMSO（少许）、甲醇（少许）
• LogP：
  2.710 (est)
• 物理描述：
  Solid
• 碰撞截面：
  163.4 Ų [M+H]+ [CCS Type: TW, Method: calibrated with polyalanine and drug standards]

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  22
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  127
• 氢给体数：
  5
• 氢受体数：
  7

安全信息

• 海关编码：
  2914501900

制备方法与用途

曲西汀是Keap1-Nrf2蛋白相互作用的有效竞争抑制剂。在帕金森病模型中，曲西汀通过激活Nrf2/HO-1信号通路并阻止线粒体依赖性凋亡通路来保护模型免受6-OHDA诱导的神经毒性。

反应信息

• 作为反应物：
  描述：

  5,7,3',4',5'-五羟基黄酮 生成 7-acetoxy-5-hydroxy-2-(3,4,5-triacetoxy-phenyl)-chromen-4-one
  参考文献：
  名称：

  CCCLXV - khapli小麦的黄色色素，小麦dicoccum

  摘要：

  DOI：

  10.1039/jr9310002624
• 作为产物：
  描述：

  (E)-1-(2-hydroxy-4,6-dimethoxyphenyl)-3-(3,4,5-trimethoxyphenyl)prop-2-en-1-one 在 氢溴酸 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 1,4-二氧六环 、 水 为溶剂， 反应 12.0h， 生成 5,7,3',4',5'-五羟基黄酮
  参考文献：
  名称：

  Unraveling the anti-influenza effect of flavonoids: Experimental validation of luteolin and its congeners as potent influenza endonuclease inhibitors

  摘要：

  The biological effects of flavonoids on mammal cells are diverse, ranging from scavenging free radicals and anti-cancer activity to anti-influenza activity. Despite appreciable effort to understand the anti-influenza activity of flavonoids, there is no clear consensus about their precise mode-of-action at a cellular level. Here, we report the development and validation of a screening assay based on AlphaScreen technology and illustrate its application for determination of the inhibitory potency of a large set of polyols against PA N-terminal domain (PA-Nter) of influenza RNA-dependent RNA polymerase featuring endonuclease activity. The most potent inhibitors we identified were luteolin with an IC₅₀ of 72 ± 2 nM and its 8-C-glucoside orientin with an IC₅₀ of 43 ± 2 nM. Submicromolar inhibitors were also evaluated by an in vitro endonuclease activity assay using single-stranded DNA, and the results were in full agreement with data from the competitive AlphaScreen assay. Using X-ray crystallography, we analyzed structures of the PA-Nter in complex with luteolin at 2.0 Å resolution and quambalarine B at 2.5 Å resolution, which clearly revealed the binding pose of these polyols coordinated to two manganese ions in the endonuclease active site. Using two distinct assays along with the structural work, we have presumably identified and characterized the molecular mode-of-action of flavonoids in influenza-infected cells.

  DOI：

  10.1016/j.ejmech.2020.112754

文献信息

• Kappa agonist compounds and pharmaceutical formulations thereof
  申请人：——

  公开号：US20030144272A1

  公开（公告）日：2003-07-31

  Compounds having kappa opioid agonist activity, compositions containing them and method of using them as analgesics are provided. The compounds of formulae I, II, IIA, III, IIIA, IIIB, IIIB-i, IV and IVA have the structure: 1 2 wherein R 1 , R 2 , R 3 , R 4 ; and X, X 4 , X 5 , X 7 , X 9 ; Y, Z and n are as described in the specification.

  提供具有kappa阿片受体激动剂活性的化合物，含有这些化合物的组合物以及使用它们作为镇痛剂的方法。 具有以下结构的化合物I、II、IIA、III、IIIA、IIIB、IIIB-i、IV和IVA： 1 2 其中 R 1 ，R 2 ，R 3 ，R 4 ；和 X，X 4 ，X 5 ，X 7 ，X 9 ； Y，Z和n如规范中所述。
• 一种三粒小麦黄酮的制备方法和应用
  申请人：常州大学

  公开号：CN110183406A

  公开（公告）日：2019-08-30

  本发明属于药物合成领域，特别涉及一种三粒小麦黄酮的制备方法和应用。以2,4,6‑三羟基苯乙酮为起始原料，经羟基保护生成化合物3，化合物3与3,4,5‑三甲氧基苯甲酰氯经酰化反应生成化合物4，化合物4经Baker‑Venkataranan重排生成化合物5，化合物5经H2SO4/HOAc催化成环生成化合物6，最后化合物6经吡啶盐酸脱保护生成三粒小麦黄酮。在合成化合物5的步骤中，选择碱为NaOH，溶剂为吡啶时收率大大提高，且反应比较稳定。经过药理活性实验表明本发明所合成的化合物具有抗神经损伤活性，使得该化合物在治疗神经损伤相关疾病具有较好的应用前景。
• Carboxamide and amino derivatives and methods of their use
  申请人：Dolle E. Roland

  公开号：US20050113294A1

  公开（公告）日：2005-05-26

  Carboxamide and amino derivatives, pharmaceutical compositions containing these compounds, and methods for their pharmaceutical use are disclosed. In certain embodiments, the carboxamide derivatives are ligands of the δ opioid receptor and are useful, inter alia, for treating and/or preventing pain, anxiety, gastrointestinal disorders, and other δ opioid receptor-mediated conditions.

  Carboxamide和氨基衍生物，含有这些化合物的药物组合物，以及其药用方法被披露。在某些实施例中，Carboxamide衍生物是δ阿片受体的配体，可用于治疗和/或预防疼痛、焦虑、胃肠道疾病和其他δ阿片受体介导的疾病。
• Inhibitory Effects of 5,6,7-Trihydroxyflavones on Tyrosinase
  作者：Hong Gao、Jun Nishida、Shizuka Saito、Jun Kawabata

  DOI：10.3390/12010086

  日期：——

  Baicalein (1), 6-hydroxyapigenin (6), 6-hydroxygalangin (13) and 6-hydroxy-kaempferol (14), which are naturally occurring flavonoids from a set of 14 hydroxy-flavones tested, exhibited high inhibitory effects on tyrosinase with respect to L-DOPA,while each of the 5,6,7-trihydroxyflavones 1, 6, 13 or 14 acted as a cofactor tomonophenolase. Moreover, 6-hydroxykaempferol (14) showed the highest activity andwas a competitive inhibitor of tyrosinase compared to L-DOPA. 5,6,7-Trihydroxyflavones 1, 6, 13 or 14 showed also high antioxidant activities. Hence, weconclude that the 5,6,7-trihydroxy-flavones are useful as good depigmentation agentswith inhibitory effects in addition to their antioxidant properties.

  从一组14种羟基黄酮中，天然存在的黄酮类化合物Baicalein（1）、6-羟基芹菜素（6）、6-羟基高良姜素（13）和6-羟基山柰酚（14）对酪氨酸酶关于L-多巴显示出高抑制效果，其中每一种5,6,7-三羟基黄酮1、6、13或14作为单酚酶的辅因子。此外，6-羟基山柰酚（14）表现出最高的活性，并且与L-多巴相比是酪氨酸酶的竞争性抑制剂。5,6,7-三羟基黄酮1、6、13或14也显示出高抗氧化活性。因此，我们得出结论，5,6,7-三羟基黄酮除了其抗氧化特性外，还具有良好的脱色素抑制效果，是有用的脱色素剂。
• Fused bicyclic carboxamide derivatives and methods of their use
  申请人：Dolle E. Roland

  公开号：US20050054630A1

  公开（公告）日：2005-03-10

  Fused bicyclic carboxamide derivatives are disclosed. Pharmaceutical compositions containing the compounds and methods for their use are also disclosed.

  揭示了融合的双环羧酰胺衍生物。还公开了含有这些化合物的药物组合物以及它们的使用方法。