5-hydroxy-3-(4-hydroxyphenyl)-7-(methoxymethoxy)-4H-chromen-4-one | 1204747-90-9

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 异黄酮类化合物
• 英文名称: 5-hydroxy-3-(4-hydroxyphenyl)-7-(methoxymethoxy)-4H-chromen-4-one
• 英文别名: 4',5-dihydroxy-7-methoxymethoxyisoflavone；5-Hydroxy-3-(4-hydroxyphenyl)-7-(methoxymethoxy)chromen-4-one
• CAS: 1204747-90-9
• 化学式: C₁₇H₁₄O₆
• 分子量: 314.295
• InChiKey: VCEVOPQFXDBINC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  85.2
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  5-hydroxy-3-(4-hydroxyphenyl)-7-(methoxymethoxy)-4H-chromen-4-one 在 盐酸 、 potassium carbonate 、 potassium iodide 作用下， 以 乙醇 、 乙腈 为溶剂， 生成 3-(4-(4-(ethyl(2-methoxybenzyl)amino)butoxy)phenyl)-5,7-dihydroxy-4H-chromen-4-one
  参考文献：
  名称：

  Design, synthesis and evaluation of genistein-O-alkylbenzylamines as potential multifunctional agents for the treatment of Alzheimer's disease

  摘要：

  A series of genistein derivatives with carbon spacer-linked alkylbenzylamines were designed, synthesized and tested as multifunctional agents for the treatment of Alzheimer's disease (AD). The results showed that most of these compounds exhibited good acetylcholinesterase (AChE) inhibitory activity, with moderate-to-good anti-oxidative activity. Specifically, compounds 10b, 19d and 254 exhibited significant inhibition of beta-amyloid (A beta) aggregation and exhibited metal chelating properties. In particular, 25d inhibited: self-induced A beta(1-42) aggregation, Cu2+-induced A beta(1-42) aggregation, and human AChE-induced A beta(1-40) aggregation by 35%, 77.8%, and 36.2%, respectively. Moreover, both kinetic analysis of AChE inhibition and the molecular modeling study suggested that 25d binds simultaneously to catalytic active site and peripheral anionic site of AChE. More importantly, compound 25d disassembled the well-structured A beta fibrils generated by Cu2+-induced A beta aggregation by 72.1%. Furthermore, the step-down passive avoidance test showed this compound significantly reversed scopolamine-induced memory deficit in mice. These results suggest that 25d may be a promising multifunctional agent for AD treatment. (C) 2014 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2014.02.045
• 作为产物：
  描述：

  染料木素 、 氯甲基甲基醚 在 potassium iodide 、 potassium hydroxide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 13.0h， 以61.5%的产率得到5-hydroxy-3-(4-hydroxyphenyl)-7-(methoxymethoxy)-4H-chromen-4-one
  参考文献：
  名称：

  Genistein-IR783 偶联物的合成和生物学评价：MCF-7 中的癌细胞靶向递送用于卓越的抗癌治疗

  摘要：

  基于类黄酮的天然产物染料木黄酮是一种生物活性化合物，具有良好的抗氧化和抗癌特性。较差的药代动力学以及低效价限制但是染料木黄酮在癌症治疗中的治疗应用。为了克服这些限制并扩大其疗效窗口，我们试图将染料木黄酮与七甲炔花青染料 - IR 783 共价连接，用于癌细胞靶向和增强向肿瘤的递送。在此，我们报告了染料木黄酮-IR 783 偶联物 4 的合成、选择性详细表征和初步体外/体内生物学评估。与相比，偶联物 4 显示出对人乳腺癌 MCF-7 细胞（10.4 ± 1.0 μM）的改进效力母体染料木素 (24.8 ± 0.5 μM) 或 IR 783 (25.7 ± 0. 7 μM)，并在各种测定中表现出与正常乳腺 MCF-10A 细胞相比在 MCF-7 中的选择性高吸收。在细胞活力测定中，偶联物 4 对 MCF-10A 细胞的效力低三倍（32.1 ± 1.1 μM），表明与染料 IR783 偶联后，母

  DOI：

  10.3390/molecules24224120

文献信息

• 一种靶向肿瘤细胞的黄酮类化合物及其制备方法
  申请人：广州中医药大学

  公开号：CN106008481A

  公开（公告）日：2016-10-12

  本发明属于有机化学领域，涉及一种靶向肿瘤细胞的黄酮类化合物，其化学结构式为下式(Ⅰ)所示。本发明所述的黄酮类化合物由异黄酮在NaH作用下和IR783反应，然后酸性条件下脱保护得到。本发明所述的黄酮类化合物抑制肿瘤细胞生长的效果显著提高。
• Novel phenoxyalkylcarboxylic acid derivatives as hypolipidaemic agents
  作者：Wei Li、Hao-yan Jia、Xin-hua He、Wei-guo Shi、Bo-hua Zhong

  DOI：10.3109/14756366.2011.589840

  日期：2012.4.1

  Novel phenoxyalkylcarboxylic acid derivatives based on the natural scaffolds, flavonoids, or resveratrol were designed, synthesized, and evaluated for hypolipidaemic activity. Among the compounds, 30b lowered the triglycerides by 48.5% (P < 0.05) and total cholesterol by 44.2% (P < 0.05), respectively, and was more effective than the reference drug fenofibric acid in a Triton WR-1339-induced hyperlipidaemic mice model orally (300 mg/kg body weight). 30b also showed 59.4% triglycerides lowering in an alloxan-induced diabetic mice model orally (150 mg/kg body weight). Receptor docking studies revealed that compound 30b could interact with the amino acid residues in the ligandbinding domain essential for the activation of the PPAR alpha. The results indicate that resveratrol should be a better scaffold to derive a new class of hypolipidaemic agents in comparison with a flavonoid scaffold.
• Synthesis and biological evaluation of genistein-<i>O</i> -alkylamine derivatives as potential multifunctional anti-Alzheimer agents
  作者：Chen Hong、Hui-yan Guo、Shuai Chen、Jian-wu Lv、Xin Zhang、Ya-cheng Yang、Kang Huang、Yi-juan Zhang、Zhi-yong Tian、Wen Luo、Yi-ping Chen

  DOI：10.1111/cbdd.13414

  日期：2019.2

  AbstractA series of genistein derivatives were synthesized and evaluated as multifunctional anti‐Alzheimer agents. The results showed that these derivatives had significant acetylcholinesterase (AChE) inhibitory activity; compound 5a exhibited the strongest inhibition to AChE with an IC50 value (0.034 μM) much lower than that of rivastigmine (6.53 μM). A Lineweaver–Burk plot and molecular modeling study showed that compound 5a targeted both the catalytic active site and the peripheral anionic site of AChE. These compounds also showed potent peroxy scavenging activity and metal‐chelating ability. The compounds did not show obvious effect on HepG2 and PC12 cell viability at the concentration of 100 μM. Therefore, these genistein derivatives can be utilized as multifunctional agents for the treatment of AD.
• The Suzuki–Miyaura Cross-Coupling–Claisen Rearrangement–Cross-Metathesis Approach to Prenylated Isoflavones
  作者：George Kwesiga、Julia Greese、Alexandra Kelling、Eric Sperlich、Bernd Schmidt

  DOI：10.1021/acs.joc.2c02698

  日期：2023.2.3