4-fluoro-2',4',6'-trihydroxychalcone | 320784-12-1

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: 4-fluoro-2',4',6'-trihydroxychalcone
• 英文别名: 3-(4-Fluorophenyl)-1-(2,4,6-trihydroxyphenyl)prop-2-en-1-one；3-(4-fluorophenyl)-1-(2,4,6-trihydroxyphenyl)prop-2-en-1-one
• CAS: 320784-12-1
• 化学式: C₁₅H₁₁FO₄
• 分子量: 274.248
• InChiKey: SHTJJLRPHGCOGK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.84
• 重原子数：
  20.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  77.76
• 氢给体数：
  3.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  4-fluoro-2',4',6'-trihydroxychalcone 在 双氧水 、 二乙胺 作用下， 以 四氢呋喃 为溶剂， 以53%的产率得到2-(4'-fluorophenyl)-3,5,7-trihydroxychroman-4-one
  参考文献：
  名称：

  二氢黄酮醇衍生物的设计，合成及抗炎活性

  摘要：

  设计并合成了三十种二氢黄酮醇衍生物（D1 - D30），同时在光谱分析的基础上对合成的化合物进行了表征。它们对脂多糖（LPS）刺激的鼠RAW 264.7巨噬细胞中促炎性诱导白介素1β（IL-1β），白介素6（IL-6）和肿瘤坏死因子-α（TNF-α）的抑制活性为评估并显示出各种效率。化合物D1 - D30在20μM的浓度下对RAW 264.7细胞无毒作用；其中，化合物D9，D13和D19通过降低IL-1β，IL-6和TNF-α表现出最佳的抗炎活性。此外，初步讨论了它们的结构-活性关系。

  DOI：

  10.1007/s00044-017-2054-z
• 作为产物：
  描述：

  1-[2-羟基-4,6-双(甲氧基甲氧基)苯基]乙酮,2',4'-双(甲氧基甲氧基)-6'-羟基苯乙酮 在 对甲苯磺酸 、 sodium hydroxide 作用下， 以 1,4-二氧六环 、 乙醇 、 二氯甲烷 、 水 为溶剂， 反应 25.0h， 生成 4-fluoro-2',4',6'-trihydroxychalcone
  参考文献：
  名称：

  作为 AKR1C3 有效抑制剂的天然查耳酮类似物

  摘要：

  天然存在的物质是药物开发的宝贵资源。在这方面，已知查耳酮通过各种机制或靶标是针对前列腺癌细胞系的抗增殖剂。根据文献和初步结果，我们旨在研究和优化一系列查耳酮抑制雄激素转化 AKR1C3 的效率，AKR1C3 已知会促进前列腺癌。总共合成了12种具有不同取代模式的查耳酮。通过进行酶测定和对接模拟，分析了与这些 AKR1C3 抑制修饰相关的结构-活性关系。此外，还评估了化合物的选择性和细胞毒性。在酶测定中，C-6'羟基化衍生物比C-6'甲氧基化衍生物活性更高。相反，C-4 甲基化比 C-4 羟基化活性更高。对接结果支持了这些发现，最活跃的化合物很好地适合结合位点，并与关键氨基酸残基表现出强烈的相互作用。最有效的抑制剂对 HEK293T 细胞没有细胞毒性，并且对主要参与类固醇激素代谢的 17β-羟基类固醇脱氢酶具有选择性。然而，它们抑制了类固醇代谢途径的几种酶。确定了增强 AKR1C3 对查耳酮

  DOI：

  10.3390/metabo12020099

文献信息

• Synthesis and studies on antidepressant activity of 2′,4′,6′-trihydroxychalcone derivatives
  作者：Xin Sui、Ying-Chun Quan、Yue Chang、Rui-Peng Zhang、Yin-Feng Xu、Li-Ping Guan

  DOI：10.1007/s00044-011-9640-2

  日期：2012.7

  In this study, we synthesized a series of 2',4',6'-trihydroxychalcone derivatives and evaluated their antidepressant activities. The results of the nine compounds showed significantly reduced times during the forced swimming test at a dose of 10 mg/kg, indicative of antidepressant activity. Among the compounds, 2-bromo-2',4',6'-trihydroxychalcone (3h) was found to be the most potent, and it was observed that compound 3h at dose of 10, 20, and 40 mg/kg significantly reduced the duration of immobility times in the FST and TST in mice 30 min after treatment.
• Potent CDC25B and PTP1B phosphatase inhibitors: 2′,4′,6′-trihydroxylchalcone derivatives
  作者：Shui-Lian Zhao、Zhou Peng、Xing-Hua Zhen、Hong-Guo Jin、Yan Han、You-Le Qu、Li-Ping Guan

  DOI：10.1007/s00044-014-1264-x

  日期：2015.6

  In this study, we examined a series of 2',4',6'-trihydroxychalcone derivatives for their inhibitory activity as inhibitors of CDC25B and PTP1B. The pharmacological results showed that all of the tested compounds significantly inhibited CDC25B and PTP1B phosphatase in vitro. Among them, three compounds 2, 6, and 7 had the best inhibition activity, with inhibition rates against CDC25B were 99.56, 99.68, and 99.63 %, respectively, and with inhibition rates against PTP1B were 98.99, 99.37, and 98.08 %, respectively, which is similar to reference drugs Na3VO4 and Oleanolic acid, respectively. Cytotoxic activity assays showed compounds 2, 6, and 7 are potent against HeLa and HCT116. Moreover, compound 6 delayed the potent antitumor inhibitory activity in a colo205 xenograft model in vivo.
• Design, synthesis and antidepressant activity evaluation 2′-hydroxy-4′,6′-diisoprenyloxychalcone derivatives
  作者：Li-Ping Guan、Dong-Hai Zhao、Yue Chang、Yu Sun、Xiao-Li Ding、Jing-Fei Jiang

  DOI：10.1007/s00044-013-0517-4

  日期：2013.11

  In this study, 14 2'-hydroxy-4',6'-diisoprenyloxychalcone compounds were synthesized and their antidepressant activities were evaluated using the forced swimming test. The pharmacological results showed that six compounds significantly reduced immobility times during the forced swimming test at a dose of 10 mg/kg, indicative of antidepressant activity. Among these, three compounds (4d, 4e, and 4g) exhibited better antidepressant activity, with reduced immobility time by 38.3, 34.0, and 27.4 %, respectively. For explanation of the putative mechanism of action, compounds 4e, 4g were tested in chemical induced models.
• Design, synthesis and anti-inflammatory activity of dihydroflavonol derivatives
  作者：Chunling Hu、Zongbao Zhou、Yuanhang Xiang、Xiaoying Song、Hong Wang、Kaiqi Tao、Xiaochuan Ye

  DOI：10.1007/s00044-017-2054-z

  日期：2018.1

  Thirty dihydroflavonol derivatives (D1–D30) were designed and synthesized, meanwhile the synthesized compounds were characterized on the basis of spectroscopic analyzes. Their inhibitory activity against the pro-inflammatory inducible interleukin-1β (IL-1β), interleukin-6 (IL-6), and tumor necrosis factor-α (TNF-α) in lipopolysaccharide (LPS)-stimulated murine RAW 264.7 macrophages were evaluated and

  设计并合成了三十种二氢黄酮醇衍生物（D1 - D30），同时在光谱分析的基础上对合成的化合物进行了表征。它们对脂多糖（LPS）刺激的鼠RAW 264.7巨噬细胞中促炎性诱导白介素1β（IL-1β），白介素6（IL-6）和肿瘤坏死因子-α（TNF-α）的抑制活性为评估并显示出各种效率。化合物D1 - D30在20μM的浓度下对RAW 264.7细胞无毒作用；其中，化合物D9，D13和D19通过降低IL-1β，IL-6和TNF-α表现出最佳的抗炎活性。此外，初步讨论了它们的结构-活性关系。
• Analogues of Natural Chalcones as Efficient Inhibitors of AKR1C3
  作者：Gabriele Möller、Veronika Temml、Antonio Cala Peralta、Océane Gruet、Pascal Richomme、Denis Séraphin、Guillaume Viault、Luisa Kraus、Petra Huber-Cantonati、Elisabeth Schopfhauser、Johanna Pachmayr、Janina Tokarz、Daniela Schuster、Jean-Jacques Helesbeux、Kenneth Allen Dyar

  DOI：10.3390/metabo12020099

  日期：——

  analysed by performing enzymatic assays and docking simulations. In addition, the selectivity and cytotoxicity of the compounds were assessed. In enzymatic assays, C-6′ hydroxylated derivatives were more active than C-6′ methoxylated derivatives. In contrast, C-4 methylation increased activity over C-4 hydroxylation. Docking results supported these findings with the most active compounds fitting nicely

  天然存在的物质是药物开发的宝贵资源。在这方面，已知查耳酮通过各种机制或靶标是针对前列腺癌细胞系的抗增殖剂。根据文献和初步结果，我们旨在研究和优化一系列查耳酮抑制雄激素转化 AKR1C3 的效率，AKR1C3 已知会促进前列腺癌。总共合成了12种具有不同取代模式的查耳酮。通过进行酶测定和对接模拟，分析了与这些 AKR1C3 抑制修饰相关的结构-活性关系。此外，还评估了化合物的选择性和细胞毒性。在酶测定中，C-6'羟基化衍生物比C-6'甲氧基化衍生物活性更高。相反，C-4 甲基化比 C-4 羟基化活性更高。对接结果支持了这些发现，最活跃的化合物很好地适合结合位点，并与关键氨基酸残基表现出强烈的相互作用。最有效的抑制剂对 HEK293T 细胞没有细胞毒性，并且对主要参与类固醇激素代谢的 17β-羟基类固醇脱氢酶具有选择性。然而，它们抑制了类固醇代谢途径的几种酶。确定了增强 AKR1C3 对查耳酮