2-(3,4-dihydroxyphenyl)-7-fluoro-3-hydroxy-4H-chromen-4-one | 1394018-41-7

• 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: 2-(3,4-dihydroxyphenyl)-7-fluoro-3-hydroxy-4H-chromen-4-one
• 英文别名: 7-fluoro-3',4'-dihydroxyflavonol；2-(3,4-Dihydroxyphenyl)-7-fluoro-3-hydroxychromen-4-one
• CAS: 1394018-41-7
• 化学式: C₁₅H₉FO₅
• 分子量: 288.232
• InChiKey: OLGKVFXSZSXZRI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  21
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  87
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  4-氟-2-羟基苯乙酮 在 双氧水 、 sodium ethanolate 、 三溴化硼 、 sodium hydroxide 作用下， 以 甲醇 、 乙醇 、 二氯甲烷 、 水 为溶剂， 反应 1.5h， 生成 2-(3,4-dihydroxyphenyl)-7-fluoro-3-hydroxy-4H-chromen-4-one
  参考文献：
  名称：

  Synthesis and biological evaluation of novel flavonols as potential anti-prostate cancer agents

  摘要：

  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.

  DOI：

  10.1016/j.ejmech.2012.06.031

文献信息

• Design, synthesis and bioactivity evaluation of fisetin derivatives as potential anti-inflammatory agents against LPS-induced acute lung injury
  作者：Xiemin Wang、Jun Yang、Bingyu Ding、Pan Chen、Zhengwei Xu、Yunxi Zhao、Pengqin Chen、Nipon Chattipakorn、Guang Liang、Di Wu、Qidong Tang

  DOI：10.1016/j.bmc.2021.116456

  日期：2021.11

  various biological activities of fisetin, we reported the design and synthesis of a series of fisetin derivatives which were also evaluated for their anti-inflammatory activities in J774A.1 macrophages. Most of the obtain derivatives could effectively inhibit the release of IL-6 and TNF-α in vitro experiments without cytotoxicity. The most promising compound 5b exhibited significant in vivo anti-inflammatory

  急性肺损伤 (ALI) 是一种由炎症引起的常见且危及生命的疾病。然而，对于 ALI，有效的药物治疗很少见。天然产物被认为是药物发现的重要来源，这表明在天然产物中寻找新的抗炎药物是一种可行的方法。受非瑟酮各种生物活性的启发，我们报道了一系列非瑟酮衍生物的设计和合成，这些衍生物还评估了它们在 J774A.1 巨噬细胞中的抗炎活性。所得衍生物大部分在体外实验中均能有效抑制IL-6和TNF-α的释放，且无细胞毒性。最有希望的化合物5b在体内表现出显着LPS 诱导的小鼠 ALI 模型中的抗炎活性。总的来说，这项研究可以为治疗 ALI 提供新的候选者。
• 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.