1-(2,4,5-trihydroxyphenyl)-2-(3,4-dimethoxyphenyl)ethanone | 66116-74-3

• 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-(2,4,5-trihydroxyphenyl)-2-(3,4-dimethoxyphenyl)ethanone
• 英文别名: 3,4-dimethoxybenzyl 2,4,5-trihydroxyphenyl ketone；2,4,5-trihydroxy-3',4'-dimethoxy-deoxybenzoin；2,4,5-Trihydroxy-3',4'-dimethoxy-desoxybenzoin；2-(3,4-Dimethoxyphenyl)-1-(2,4,5-trihydroxyphenyl)ethan-1-one；2-(3,4-dimethoxyphenyl)-1-(2,4,5-trihydroxyphenyl)ethanone
• CAS: 66116-74-3
• 化学式: C₁₆H₁₆O₆
• 分子量: 304.299
• InChiKey: XENYBVPCIRWTMR-UHFFFAOYSA-N

物化性质

• 熔点：
  193–194°C

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.19
• 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-(2,4,5-trihydroxyphenyl)-2-(3,4-dimethoxyphenyl)ethanone 生成 1-(2-hydroxy-4,5-dimethoxyphenyl)-2-(3,4-dimethoxyphenyl)ethanone
  参考文献：
  名称：

  JAIN, AMOLAK C.;PRASAD, ASHOK K., INDIAN J. CHEM. B, 27,(1988) N 7, C. 622-624

  摘要：

  DOI：
• 作为产物：
  描述：

  以 水 为溶剂， 反应 2.0h， 生成 1-(2,4,5-trihydroxyphenyl)-2-(3,4-dimethoxyphenyl)ethanone
  参考文献：
  名称：

  Jain, Amolak C.; Prasad, Ashok K., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1988, vol. 27, # 1-12, p. 622 - 624

  摘要：

  DOI：

文献信息

• 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。
• Anjaneyulu; Rajagopalan, Proceedings - Indian Academy of Sciences, Section A, 1959, # 50, p. 219,222
  作者：Anjaneyulu、Rajagopalan

  DOI：——

  日期：——
• ISOFLAVANS DERIVATIVES AS INHIBITORS OF SOYBEAN LIPOXYGENASE: IN-VITRO AND DOCKING STUDIES
  作者：CAROLINA MASCAYANO、MARCOS CAROLI REZENDE、YENIFER RIVERA、VICTORIA ESPINOSA

  DOI：10.4067/s0717-97072011000400024

  日期：——

  The lipoxygenases (LOX) are a family of non-heme iron-containing dioxygenases which catalyze the stereospecific insertion of molecular oxygen lino arachidonic acid, leading to hydroxy derivatives as end products. In this work, we studied the behavior of seven isoflavans on 15-soybean lipoxygenases (15-sLOX), comparing them with the known inhibitors quercetin and 3,4-dihydroxybenzoic acid. Four of the seven investigated isoflavans showed IC50 values smaller than 50 mu M, being more potent than quercetin or 3, 4-dihydroxybenzoic acid. Besides a catecholic pattern, the presence of an aromatic ring B seems to confer additional activity to these compounds, a result which was rationalized by docking studies of these isoflavanss into the enzyme binding site.
• JAIN, AMOLAK C.;PRASAD, ASHOK K., INDIAN J. CHEM. B, 27,(1988) N 7, C. 622-624
  作者：JAIN, AMOLAK C.、PRASAD, ASHOK K.

  DOI：——

  日期：——
• Jain, Amolak C.; Prasad, Ashok K., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1988, vol. 27, # 1-12, p. 622 - 624
  作者：Jain, Amolak C.、Prasad, Ashok K.

  DOI：——

  日期：——