3-hydroxy-2-(3-hydroxy-4-methoxyphenyl)-4H-chromen-4-one | 1621-74-5

• 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-(3-hydroxy-4-methoxyphenyl)-4H-chromen-4-one
• 英文别名: 3'-Hydroxy-4'-methoxy-flavonol；3-Hydroxy-2-(3-hydroxy-4-methoxyphenyl)chromen-4-one；3-hydroxy-2-(3-hydroxy-4-methoxyphenyl)chromen-4-one
• CAS: 1621-74-5
• 化学式: C₁₆H₁₂O₅
• 分子量: 284.268
• InChiKey: LJHOYEXLNJWJDE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 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

• 作为产物：
  描述：

  2'-羟基苯乙酮 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-(3-hydroxy-4-methoxyphenyl)-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

• Design, synthesis and biological activity of flavonoid derivatives as selective agonists for neuromedin U 2 receptor
  作者：Ming-Liang Ma、Ming Li、Jiao-Jiao Gou、Tian-Yu Ruan、Hai-Shan Jin、Ling-Hong Zhang、Liang-Chun Wu、Xiao-Yan Li、Ying-He Hu、Ke Wen、Zheng Zhao

  DOI：10.1016/j.bmc.2014.08.038

  日期：2014.11

  Central neuromedin U 2 receptor (NMU2R) plays important roles in the regulation of food intake and body weight. Identification of NMU2R agonists may lead to the development of pharmaceutical agents to treat obesity. Based on the structure of rutin, a typical flavonoid and one of the NMU2R agonists we previously identified from an in-house made natural product library, 30 flavonoid derivatives have been synthesized and screened on a cell-based reporter gene assay. A number of compounds were found to be selective and highly potent to NMU2R. For example, the EC50 value of compound NRA 4 is very close to that of NMU, the endogenous peptide ligand of NMU2R. Structure-activity relationship analysis revealed that a 3-hydroxyl group in ring C and a 2'-fluoride group in ring B were essential for this class of compounds to be active against NMU2R. (C) 2014 Elsevier Ltd. All rights reserved.
• UTILISATION D'UNE ASSOCIATION DE DEUX COMPOSÉS POUR LE TRAITEMENT ET/OU LA PRÉVENTION DE TROUBLES OSSEUX
  申请人：Institut National de la Recherche Agronomique (INRA)

  公开号：EP2999467B1

  公开（公告）日：2020-01-08
• [EN] USE OF A COMBINATION OF TWO COMPOUNDS FOR THE TREATMENT AND/OR PREVENTION OF BONE DISORDERS<br/>[FR] UTILISATION D'UNE ASSOCIATION DE DEUX COMPOSÉS POUR LE TRAITEMENT ET/OU LA PRÉVENTION DE TROUBLES OSSEUX
  申请人：AGRONOMIQUE INST NAT RECH

  公开号：WO2014184484A1

  公开（公告）日：2014-11-20

  L'invention concerne une association comprenant au moins (i) la fisétine, ou l'un de ses dérivés, et (ii) l'acide docosahexaénoïque (DHA), ou l'un de ses dérivés, pour son utilisation pour le traitement et/ou la prévention de troubles associés à une perte osseuse et/ou à un déséquilibre du rapport entre la formation et la résorption osseuse. L'invention concerne également une composition comprenant ladite association pour son utilisation telle que décrite précédemment.
• 3′-Hydroxy-3,4′-dimethoxyflavone blocks tubulin polymerization and is a potent apoptotic inducer in human SK-MEL-1 melanoma cells
  作者：Francisco Estévez-Sarmiento、Mercedes Said、Ignacio Brouard、Francisco León、Celina García、José Quintana、Francisco Estévez

  DOI：10.1016/j.bmc.2017.09.043

  日期：2017.11

  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.