1-(3,6-二羟基-2-甲氧基苯基)乙酮 | 33539-20-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 1-(3,6-二羟基-2-甲氧基苯基)乙酮
• 英文名称: 2,5-dihydroxy-6-methoxyacetophenone
• 英文别名: 3',6'-dihydroxy-2'-methoxyacetophenone；1-(3,6-Dihydroxy-2-methoxyphenyl)ethanone
• CAS: 33539-20-7
• 化学式: C₉H₁₀O₄
• mdl: MFCD11109166
• 分子量: 182.176
• InChiKey: WXOYSNLFYSJUDB-UHFFFAOYSA-N

物化性质

• 熔点：
  91°C

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.222
• 拓扑面积：
  66.8
• 氢给体数：
  2
• 氢受体数：
  4

安全信息

• 海关编码：
  2914509090

反应信息

• 作为反应物：
  描述：

  1-(3,6-二羟基-2-甲氧基苯基)乙酮 在 potassium carbonate 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 丙酮 为溶剂， 反应 2.67h， 生成 6-(3-chloro-benzyloxy)-5-methoxy-2-methylsulfanyl-chromen-4-one
  参考文献：
  名称：

  2,6-Bis-arylmethyloxy-5-hydroxychromones with antiviral activity against both hepatitis C virus (HCV) and SARS-associated coronavirus (SCV)

  摘要：

  In this study, as a bioisosteric alternative scaffold of the antiviral aryl diketoacids (ADKs), we used 5-hydroxychromone on which two arylmethyloxy substituents were installed. The 5-hydroxychromones (5b-5g) thus prepared showed anti-HCV activity and, depending on the aromatic substituents on the 2-arylmethyloxy moiety, some of the derivatives (5b-5f) were also active against SCV. In addition, unlike the ADKs which showed selective inhibition against the helicase activity of the SCV NTPase/helicase, the 5-hydroxychromones (5b-5f) were active against both NTPase and helicase activities of the target enzyme. Among those, 3-iodobenzyloxy-substituted derivative 5e showed the most potent activity against HCV (EC50 = 4 mu M) as well as SCV (IC50 = 4 mu M for ATPase activity, 11 mu M for helicase activity) and this might be used as a platform structure for future development of the multi-target or broad-spectrum antivirals. (C) 2011 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2011.09.005
• 作为产物：
  描述：

  8-乙酰基-7-羟基-4-甲基-2H-1-苯并吡喃-2-酮 在 sodium hydroxide 、 dipotassium peroxodisulfate 作用下， 生成 1-(3,6-二羟基-2-甲氧基苯基)乙酮
  参考文献：
  名称：

  Wallenfels, Chemische Berichte, 1942, vol. 75, p. 785,792

  摘要：

  DOI：

文献信息

• 5-Hydroxy-6,2′-dimethoxyflavone from Primula denticulata
  作者：Eckhard Wollenweber、Munekazu Iinuma、Toshiyuki Tanaka、Mizuo Mizuno

  DOI：10.1016/0031-9422(90)85132-y

  日期：1990.1

  2′-dimethoxyflavone, was isolated from the leaf exudate of Primula denticulata . Its structure was elucidated by spectral studies and confirmed by synthesis. This flavone shows unusual fragments in its mass spectrum which is caused by the stability of the molecular ion and a new fragmentation pattern is proposed. The structure of 5,6,2′-trimethoxyflavone, reported earlier from Sargentia greggii , is also

  摘要 从报春花(Primula denticulata) 的叶分泌物中分离出一种新型的天然黄酮5-羟基-6,2'-二甲氧基黄酮。其结构通过光谱研究阐明并通过合成证实。该黄酮在其质谱中显示出异常碎片，这是由分子离子的稳定性引起的，并提出了一种新的碎片模式。早先从 Sargentia greggii 报道的 5,6,2'-三甲氧基黄酮的结构也通过合成得到证实。对报春花分泌物中发现的所有黄酮进行了调查。
• Two new methoxylated flavones isolated from <i>Casimiroa edulis</i> La Llave and their MMP-9 inhibitory activity
  作者：Manami Haba、Naohito Abe、Tetsuro Kamiya、Nagisa Mizuno、Satoshi Okubo、Takao Yamaura、Hirokazu Hara、Masayoshi Oyama

  DOI：10.1080/14786419.2022.2048300

  日期：2022.12.2

  casedulones A (1) and B (2), together with 12 known analogues. Their unique structures were established with the aid of spectral analyses and total syntheses. Pre-treatment with 20 µM of 1 and 2 suppressed MMP-9 expression in LPS-mediated THP-1 cells, indicating that the characteristic flavonoids in C. edulis could be potential anti-angiogenics for cancer prevention.

  摘要 众所周知， Casimiroa edulis La Llave 含有不寻常的 5,6-二甲氧基黄酮，带有不同氧化的 B 环。对C. edulis的叶子和根的植物化学研究实现了两种新的甲氧基化黄酮的分离，命名为 casedulones A ( 1 ) 和 B ( 2 )，以及 12 种已知的类似物。它们独特的结构是在光谱分析和全合成的帮助下建立的。用 20 µM 的1和2进行预处理可抑制 LPS 介导的 THP-1 细胞中的 MMP-9 表达，表明C. edulis中的特征类黄酮可能是预防癌症的潜在抗血管生成剂。
• 2-Arylmethylaminomethyl-5,6-dihydroxychromone derivatives with selective anti-HCV activity
  作者：Hye Ri Park、Kwang-Su Park、Youhoon Chong

  DOI：10.1016/j.bmcl.2011.04.055

  日期：2011.6

  elements, α,β-diketo acid moiety and substituted aryl ring. In this study, as a part of our ongoing efforts to discover a novel anti-HCV compound mimicking the ADK scaffold, we designed 2-arylmethylaminomethyl-5,6-dihydroxychromone derivatives of which the dihydroxychromone moiety as well as the arylmethylaminomethyl substituent (R-PhCH2NHCH2–) were anticipated in exact match with the pharmacophore model

  芳基二酮酸（ADK）的抗HCV活性已通过其两个药效学元素（α，β-二酮酸部分和取代的芳基环）进行了表征。在这项研究中，作为我们不断努力探索模仿ADK支架的新型抗HCV化合物的一部分，我们设计了2-芳基甲基氨基甲基-5,6-二羟基色酮衍生物，其中的二羟基色酮部分以及芳基甲基氨基甲基取代基（R-预计PhCH 2 NHCH 2 –）与ADK的药效团模型完全匹配。如此制得的二羟基色酮衍生物（3a – 3u）以取代基依赖性方式表现出生物活性，从而导致选择性的抗HCV效应（EC 50  = 2.0–14.0μM，CC 50 > 100μM），尤其在芳环的3位带有取代基，如Cl，Br，I和Me。
• A New and Facile Iodine(III)-Mediated Approach for the Regioselective Alkoxylation of 2,5-Dihydroxyacetophenone
  作者：Om Prakash、Rashmi Pundeer、Harpreet Kaur

  DOI：10.1055/s-2003-42461

  日期：——

  Oxidation of 2,5-dihydroxyacetophenone with iodobenzene diacetate (IBD) in different alcohols leads to regioselective alkoxylation. thereby providing a new and convenient route for the synthesis of 6-alkoxy-2,5-dihydroxyacetophenones.

  在不同的醇中用碘苯二乙酸酯 (IBD) 氧化 2,5-二羟基苯乙酮会导致区域选择性烷氧基化。从而为6-烷氧基-2,5-二羟基苯乙酮的合成提供了一条新的便捷途径。
• CHEMOTHERAPEUTIC FLAVONOIDS, AND SYNTHESES THEREOF
  申请人：Cushman Mark S.

  公开号：US20100099755A1

  公开（公告）日：2010-04-22

  Substituted flavonoid compounds, and pharmaceutical formulations of flavonoid compounds are described. Also described are processes for preparing flavonid compounds, as are methods for treating cancer in mammals using the described flavonoid compounds or pharmaceutical formulations thereof.

  本文描述了替代黄酮类化合物和黄酮类化合物的药物配方。还描述了制备黄酮类化合物的过程，以及使用所述黄酮类化合物或其药物配方治疗哺乳动物癌症的方法。