6-fluoro-3-hydroxy-2-(3,4,5-trimethoxyphenyl)-4H-chromen-4-one | 1394018-30-4

• 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: 6-fluoro-3-hydroxy-2-(3,4,5-trimethoxyphenyl)-4H-chromen-4-one
• 英文别名: 6-fluoro-3',4',5'-trimethoxyflavonol；6-Fluoro-3-hydroxy-2-(3,4,5-trimethoxyphenyl)chromen-4-one
• CAS: 1394018-30-4
• 化学式: C₁₈H₁₅FO₆
• 分子量: 346.312
• InChiKey: ZAUOVNJAOIUIRE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  25
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  74.2
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  5'-fluoro-2'-hydroxy-3,4,5-trimethoxy-chalcone 在 双氧水 、 potassium hydroxide 作用下， 以 甲醇 为溶剂， 反应 0.17h， 生成 6-fluoro-3-hydroxy-2-(3,4,5-trimethoxyphenyl)-4H-chromen-4-one
  参考文献：
  名称：

  Synthesis, inverse docking-assisted identification and in vitro biological characterization of Flavonol-based analogs of fisetin as c-Kit, CDK2 and mTOR inhibitors against melanoma and non-melanoma skin cancers

  摘要：

  DOI：

  10.1016/j.bioorg.2020.104595

文献信息

• Synthesis and biological evaluation of novel flavonols as potential anti-prostate cancer agents
  作者：Robert G. Britton、Emma Horner-Glister、Odette A. Pomenya、Ewan E. Smith、Roanne Denton、Paul R. Jenkins、William P. Steward、Karen Brown、Andreas Gescher、Stewart Sale

  DOI：10.1016/j.ejmech.2012.06.031

  日期：2012.8

  A library of flavonol analogues was synthesised and evaluated as potential anticancer agents against a human prostate cancer cell line, 22rv1. Compounds 3, 8 and 11 (IC50 2.6, 3.3 and 4.0 mu M respectively) showed potent cancer cell growth inhibition, comparable to the lead compound 3',4',5'-trimethoxyflavonol (1) (IC50 3.1 mu M) and superior to the naturally occurring flavonols quercetin (16) and fisetin (22) (both >15 mu M). Results indicate that the 3',4',5'- arrangement of either hydroxy (OH) or methoxy (OMe) residues is important for growth arrest of these cells and that the OMe analogues may be superior to their OH counterparts. Compounds 1, 3, 8 and 11 warrant further investigation as potential agents for the management of prostate cancer. (C) 2012 Elsevier Masson SAS. All rights reserved.
• Synthesis, inverse docking-assisted identification and in vitro biological characterization of Flavonol-based analogs of fisetin as c-Kit, CDK2 and mTOR inhibitors against melanoma and non-melanoma skin cancers
  作者：Tithi Roy、Samuel T. Boateng、Sergette Banang-Mbeumi、Pankaj K. Singh、Pratik Basnet、Roxane-Cherille N. Chamcheu、Federico Ladu、Isabel Chauvin、Vladimir S. Spiegelman、Ronald A. Hill、Konstantin G. Kousoulas、Bolni Marius Nagalo、Anthony L. Walker、Jean Fotie、Siva Murru、Mario Sechi、Jean Christopher Chamcheu

  DOI：10.1016/j.bioorg.2020.104595

  日期：2021.2