1-(2,4,6-trihydroxyphenyl)-2-(3,4-methylenedioxyphenyl)ethanone | 39548-98-6

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: 1-(2,4,6-trihydroxyphenyl)-2-(3,4-methylenedioxyphenyl)ethanone
• 英文别名: 2-(benzo[d][1,3]dioxol-5-yl)-1-(2,4,6-trihydroxyphenyl)ethanone；2-(1,3-benzodioxol-5-yl)-1-(2,4,6-trihydroxyphenyl)ethanone；2,4,6-trihydroxy-3',4'-methylenedioxy-deoxybenzoin；2,4,6-Trihydroxy-3',4'-methylendioxy-desoxybenzoin；2,4,6-Trihydroxy-3',4'-methylenedioxydesoxybenzoin
• CAS: 39548-98-6
• 化学式: C₁₅H₁₂O₆
• 分子量: 288.257
• InChiKey: BCRLDYNWYPWZQF-UHFFFAOYSA-N

物化性质

• 熔点：
  202°C
• 沸点：
  504.5±45.0 °C(Predicted)
• 密度：
  1.532±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  96.2
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  1-(2,4,6-trihydroxyphenyl)-2-(3,4-methylenedioxyphenyl)ethanone 在 三氯化铝 、 sodium 、 potassium carbonate 、 硝基苯 、 丙酮 、 硫酸二甲酯 作用下， 生成 3-(3,4-二羟基苯基)-5-羟基-7-甲氧基-4H-1-苯并吡喃-4-酮
  参考文献：
  名称：

  Iyer et al., Proceedings - Indian Academy of Sciences, Section A, 1951, # 33, p. 228,230

  摘要：

  DOI：
• 作为产物：
  描述：

  2-(2-(benzo[d][1,3]dioxol-5-yl)-1-iminoethyl)benzene-1,3,5-triol 在 盐酸 作用下， 反应 3.0h， 以95%的产率得到1-(2,4,6-trihydroxyphenyl)-2-(3,4-methylenedioxyphenyl)ethanone
  参考文献：
  名称：

  Synthesis and Evaluation of Derrubone and Select Analogues

  摘要：

  [GRAPHICS]Recently, we reported that the natural product derrubone exhibits Hsp90 inhibitory activity. Due to its unique architectural scaffold and proposed rapid assembly, the synthesis of this natural product was pursued with the aim of identifying structure-activity relationships. Synthesis of the natural product was accomplished in eight highly convergent steps, which led to a facile method for the construction of related compounds. Biological evaluation of derrubone and its analogues identified several compounds that exhibit low micromolar inhibitory activity against breast and colon cancer cell lines.

  DOI：

  10.1021/jo702366g

文献信息

• A Direct Synthesis of 2‐(ω‐Carboxyalkyl)isoflavones from <i>ortho</i> ‐Hydroxylated Deoxybenzoins
  作者：Galyna P. Mrug、Bohdan A. Demydchuk、Svitlana P. Bondarenko、Vitaliy M. Sviripa、Przemyslaw Wyrebek、James L. Mohler、Michael V. Fiandalo、Chunming Liu、Mykhaylo S. Frasinyuk、David S. Watt

  DOI：10.1002/ejoc.201801171

  日期：2018.10.24

  The base‐catalyzed chromone ring‐closure reaction was developed for one‐step synthesis of various 2‐(ω‐carboxyalkyl)isoflavones bearing electron‐donating and electron‐withdrawing groups.

  开发了碱催化的色酮闭环反应，用于一步合成具有供电子基团和吸电子基团的各种2-（ω-羧基烷基）异黄酮。
• Structure–Activity Relationship Prediction‐Based Synthesis and Cytotoxicity Evaluation against the HEp‐2 Laryngeal Carcinoma Cell of Isoflavone–Cytisine Mannich Bases
  作者：Galyna Mrug、Diana Hodyna、Larysa Metelytsia、Vasyl Kovalishyn、Olena Trokhimenko、Svitlana Bondarenko、Kostyantyn Kondratyuk、Andriy Kozitskiy、Mykhaylo Frasinyuk

  DOI：10.1002/cbdv.202300560

  日期：2023.8

  web platform. The validation of the models using an external test set proved that the models can be used to predict the activity of newly designed compounds such as 8-cytisinylmethyl derivatives of 5,7- and 6,7-dihydroxyisoflavones. The synthetic procedure for selective aminomethylation of 5,7-dihydroxyisoflavones with cytisine was developed. In vitro testing identified compound 7 f with cisplatin-level

  使用 OCHEM 网络平台对先前合成的、受自然启发的虚拟异黄酮-金雀花碱杂交体针对 HEp-2 喉癌细胞系进行 QSAR 分析。使用外部测试集对模型进行的验证证明，该模型可用于预测新设计的化合物的活性，例如5,7-和6,7-二羟基异黄酮的8-金雀花酰甲基衍生物。开发了金雀花碱选择性氨甲基化 5,7-二羟基异黄酮的合成方法。体外测试发现化合物7f对 HEp-2 细胞系具有顺铂水平的细胞毒性，而化合物10在孵育 72 小时后其活性是顺铂的两倍。
• Baker et al., Journal of the Chemical Society, 1953, p. 1852,1856
  作者：Baker et al.

  DOI：——

  日期：——
• Gilbert et al., Journal of the Chemical Society, 1957, p. 3740,3745
  作者：Gilbert et al.

  DOI：——

  日期：——
• [EN] FLAVONOID PPAR AGONISTS<br/>[FR] AGONISTES FLAVONOÏDES DE PPAR
  申请人：UNIV SYDNEY

  公开号：WO2009026657A1

  公开（公告）日：2009-03-05

  The present invention relates to PPAR agonists, and their use in therapy including the treatment of disease. In particular, the invention relates to flavonoid compounds which are PPAR-gamma agonists and/or PPAR alpha/gamma dual agonists.