3-hydroxy-2-(4-hydroxyphenyl)-7-methoxy-4H-chromen-4-one | 84638-53-9

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 黄酮类化合物
• 英文名称: 3-hydroxy-2-(4-hydroxyphenyl)-7-methoxy-4H-chromen-4-one
• 英文别名: 5-Deoxyrhamnocitrin；3-hydroxy-2-(4-hydroxyphenyl)-7-methoxychromen-4-one
• CAS: 84638-53-9
• 化学式: C₁₆H₁₂O₅
• 分子量: 284.268
• InChiKey: UAESYLAPUNIHOF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  76
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-hydroxy-2-(4-hydroxyphenyl)-7-methoxy-4H-chromen-4-one 、 乙酸酐 在 吡啶 作用下， 生成 3-acetoxy-2-(4-acetoxy-phenyl)-7-methoxy-chromen-4-one
  参考文献：
  名称：

  Anand et al., Proceedings - Indian Academy of Sciences, Section A, 1949, # 29, p. 203,207

  摘要：

  DOI：
• 作为产物：
  描述：

  丹皮酚 在 palladium 10% on activated carbon 、 氢气 、 双氧水 、 potassium hydroxide 、 sodium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 水 为溶剂， 反应 1.0h， 生成 3-hydroxy-2-(4-hydroxyphenyl)-7-methoxy-4H-chromen-4-one
  参考文献：
  名称：

  3′-Hydroxy-3,4′-dimethoxyflavone blocks tubulin polymerization and is a potent apoptotic inducer in human SK-MEL-1 melanoma cells

  摘要：

  Flavonoids are naturally occurring polyphenolic compounds and are among the most promising anticancer agents. A series of flavonols and their 3-methyl ether derivatives were synthesized and assessed for cytotoxicity. It was found that 3'-hydroxy-3,4'-dimethoxyflavone (flavonoid 7a) displayed strong cytotoxicity against human SK-MEL-1 melanoma cells and blocked tubulin polymerization, but had no significant cytotoxic effects against quiescent or proliferating human peripheral blood mononuclear cells. Our analyses showed that flavonoid 7a induces G2-M cell cycle arrest and apoptosis in melanoma cells which is associated with cytochrome c release and activation of both extrinsic and intrinsic apoptotic pathways of cell death. (C) 2017 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2017.09.043

文献信息

• Synthesis of Flavonols via Pyrrolidine Catalysis: Origins of the Selectivity for Flavonol versus Aurone
  作者：Wei Xiong、Xiaohong Wang、Xianyan Shen、Cuifang Hu、Xin Wang、Fei Wang、Guolin Zhang、Chun Wang

  DOI：10.1021/acs.joc.0c01869

  日期：2020.10.16

  method for flavonol from 2′-hydroxyl acetophenone and benzaldehyde promoted by pyrrolidine under an aerobic condition in water is established. This protocol was supported by efficient synthesis of 44 common examples and three natural products. The α, β-unsaturated iminium ion (enimine ion E) was proved to be the key intermediate in the reaction. H218O and 18O2 isotope tracking experiments demonstrated

  建立了一种在水中好氧条件下由吡咯烷促进的2'-羟基苯乙酮和苯甲醛合成黄酮醇的新方法。该协议得到44个常见实例和三种天然产物的有效合成的支持。事实证明，α，β-不饱和亚胺离子（亚胺离子E）是反应的关键中间体。H 2 18 O和18 O 2同位素跟踪实验表明，水和好氧气氛对于确保转化都必不可少。黄酮醇或金酮的选择性源自溶剂触发的中间体，该中间体由分离的亚胺的紫外可见光谱确定。酚亚胺EA在水中占主导地位，酮烯胺中间体EB在乙腈中盛行。在环化和[2 + 2]氧化的关键步骤之后，在吡咯烷和氧的存在下，EA通过EI（两性离子样的酚氧基亚胺离子）通过EI生成黄酮醇。EB通过路径II进行，这是由EB与吡咯烷和氧气共同光解而引发的自由基过程，从而生成金酮。初步的机械研究报道。
• Oxygenation of 4-hydroxychalcones catalysed by peroxidase and by light
  作者：Edmon Wong

  DOI：10.1016/0031-9422(89)85045-9

  日期：——

  Abstract Peroxidase or light catalysed oxygenation of 2′,4-dihydroxy-4′-methoxychalcone produced two labile initial products characterized as stereoisomers of 4′-hydroxy-6-methoxy-2-(α-hydroperoxybenzyl) coumaranone. By analogy, the products from similar oxygenation reactions of 2′,4,4′-trihydroxychalcone previously studied are now considered to be hydroperoxy-benzylcoumaranones rather than dioxetanes

  摘要 过氧化物酶或 2',4-二羟基-4'-甲氧基查尔酮的光催化氧化产生两种不稳定的初始产物，其特征为 4'-羟基-6-甲氧基-2-（α-氢过氧苄基）香豆酮的立体异构体。以此类推，之前研究的 2',4,4'-三羟基查尔酮的类似氧化反应的产物现在被认为是氢过氧苄基香豆酮而不是二氧杂环丁烷。
• Anand; Iyer; Venkataraman, Proceedings - Indian Academy of Sciences, Section A, 1949, vol. 29, p. 203,207
  作者：Anand、Iyer、Venkataraman

  DOI：——

  日期：——
• Exploration of Pharmacophore in Chrysosplenol C as Activator in Ventricular Myocyte Contraction
  作者：Eeda Venkateswararao、Min-Jeong Son、Niti Sharma、Manoj Manickam、PullaReddy Boggu、Young Ho Kim、Sun-Hee Woo、Sang-Hun Jung

  DOI：10.1021/acsmedchemlett.5b00043

  日期：2015.7.9

  Chrysosplenol C (4',5,6-trihydroxy-3,3',7-tri-methoxyflavone) isolated from Miliusa balansae has unique structural features as a reversible inotropic agent independent of beta-adrenergic signaling and with selective activation of cardiac myosin ATPase. Hence, a series of chrysosplenol analogues were synthesized and explored for identification of pharmacophore that is essential for the increasing contractility in rat ventricular myocytes. Analogue 7-chloro-2-(3-hydroxypheny1)-3-methoxy-4H-chromen-4-one showed highly potent contractility (54.8% at 10 mu M) through activating cardiac myosin ATPase (38.7% at 10 mu M). Our systematic structure activity relationship study revealed that flavonoid nucleus of chrososplenol C appears to be an essential basic skeleton and hydrophobic substituent at position 7 of chromenone such as methoxy or chloro enhances the activity. Additionally, our ATPase study suggested that these chrysosplenol analogues have selectivity toward cardiac myosin activation. Thus, the novel flavonone with 3-/7-hydrophobic substituent and 3'-hydrogen bonding donor function is a novel scaffold for discovery of a new positive inotropic agent.
• 905. Chelate systems. Part I
  作者：T. H. Simpson、Linda Garden

  DOI：10.1039/jr9520004638

  日期：——