3-hydroxy-2-(4-(trifluoromethyl) phenyl)-4H-chromen-4-one | 104197-22-0

• 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-(4-(trifluoromethyl) phenyl)-4H-chromen-4-one
• 英文别名: 4'-Trifluoromethylflavonol；4-Trifluoromethylflavonol；3-hydroxy-2-[4-(trifluoromethyl)phenyl]chromen-4-one
• CAS: 104197-22-0
• 化学式: C₁₆H₉F₃O₃
• 分子量: 306.241
• InChiKey: ZMWMRAOCJSBYPY-UHFFFAOYSA-N

物化性质

• 沸点：
  390.8±42.0 °C(Predicted)
• 密度：
  1.473±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  22
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  3-hydroxy-2-(4-(trifluoromethyl) phenyl)-4H-chromen-4-one 在 四丁基溴化铵 、 sodium methylate 、 potassium carbonate 作用下， 以 甲醇 、 二氯甲烷 、 水 为溶剂， 反应 1.0h， 生成 4′-trifluoromethylflavonyl β-D-glucopyranoside
  参考文献：
  名称：

  4'-取代基对基于黄酮醇的 β-糖苷酶活性荧光指示剂效率的影响。

  摘要：

  本文介绍了基于激发态分子内质子转移 (ESIPT) 现象和黄酮醇对特定糖苷酶的作用敏感的新型荧光探针。使用各种方法合成 4'-取代的黄酮醇，并用D-葡萄糖、N-乙酰基-D-葡萄糖胺和D-葡萄糖醛酸。β-糖苷酶活性的评估在中性和酸性 pH 值下进行。在所有检查的情况下，酸性环境加速了酶水解。已经证明，在中性和酸性 pH 值下，所有测试糖的 4'-氯黄酮苷对水解酶的存在最敏感。反过来，4'-二甲基氨基黄酮基葡糖苷对葡糖苷酶的作用完全不敏感。通常，酶水解的速率随着 4'-取代基的吸电子性质的增加而增加。一个例外是三氟甲基，尽管它具有最有利的哈米特常数，但对提高其葡糖苷的水解速率的贡献不足。

  DOI：

  10.1039/d0ob01505a
• 作为产物：
  描述：

  (E)-1-(2-hydroxyphenyl)-3-(4-(trifluoromethyl)phenyl)prop-2-en-1-one 在 sodium hydroxide 、 双氧水 作用下， 以 甲醇 为溶剂， 生成 3-hydroxy-2-(4-(trifluoromethyl) phenyl)-4H-chromen-4-one
  参考文献：
  名称：

  Srivastava; Sukhwal, Sudha; Ashawa, Anjana, Journal of the Indian Chemical Society, 1997, vol. 74, # 7, p. 573 - 574

  摘要：

  DOI：

文献信息

• Exploration of synthetic antioxidant flavonoid analogs as acetylcholinesterase inhibitors: an approach towards finding their quantitative structure–activity relationship
  作者：Abhijit Karmakar、Pravin Ambure、Tamanna Mallick、Sreeparna Das、Kunal Roy、Naznin Ara Begum

  DOI：10.1007/s00044-019-02330-8

  日期：2019.5

  acetylcholinesterase (AChE) and a series of antioxidant flavonoid analogs were studied by fluorescence spectroscopic assay. The present study incorporated different classes of naturally occurring and synthetic flavonoid compounds like flavones, isoflavones, and chalcones as well as a few standard antioxidants. The AChE inhibitory (AChEI) activity of these compounds was further analyzed using in silico techniques

  通过荧光光谱法研究了乙酰胆碱酯酶（AChE）与一系列抗氧化剂类黄酮类似物之间的结合相互作用。本研究纳入了不同种类的天然和合成类黄酮化合物，例如黄酮，异黄酮和查耳酮以及一些标准的抗氧化剂。使用计算机技术进一步分析了这些化合物的AChE抑制（AChEI）活性，即药效团作图，定量构效关系（QSAR）分析和分子对接研究。我们还比较了这些化合物的AChE抑制和自由基清除抗氧化活性。这些化合物的AChE抑制和抗氧化活性都高度依赖于其结构模式。但是，据观察，一般而言，
• Enantioselective Synthesis of 3,4-Chromanediones via Asymmetric Rearrangement of 3-Allyloxyflavones
  作者：Jean-Charles Marié、Yuan Xiong、Geanna K. Min、Adam R. Yeager、Tohru Taniguchi、Nina Berova、Scott E. Schaus、John A. Porco

  DOI：10.1021/jo100889c

  日期：2010.7.2

  Asymmetric scandium(III)-catalyzed rearrangement of 3-allyloxyflavones was utilized to prepare chiral, nonracemic 3,4-chromanediones in high yields and enantioselectivities. These synthetic intermediates have been further elaborated to novel heterocyclic frameworks including angular pyrazines and dihydropyrazines. The absolute configuration of rearrangement products was initially determined by a nonempirical

  利用不对称钪 (III) 催化的 3-烯丙氧基黄酮重排以高产率和对映选择性制备手性、非外消旋 3,4-色二酮。这些合成中间体已被进一步细化为新型杂环骨架，包括角吡嗪和二氢吡嗪。重排产物的绝对构型最初是通过圆二色性 (CD) 的非经验分析使用时间相关密度泛函理论 (TDDFT) 计算确定的，并通过腙衍生物的 X 射线晶体学验证。该机制的初步研究支持可能通过苯并吡喃中间体进行的分子内重排途径。
• Design, synthesis, and antifungal activity of flavonoid derivatives containing thiazole moiety
  作者：Fei Meng、Zixin Yan、Yuexiao Lu、Xiaobin Wang

  DOI：10.1007/s11696-022-02522-4

  日期：2023.2

  A series of flavonoid derivatives containing thiazole scaffold were designed, synthesized and evaluated for their inhibition effects against Rhizoctonia solani, Fusarium graminearum, Gaeumannomyces graminis, Alternaria solani, Botrytis cinerea, and Alternaria mali. The antifungal bioassays results in vitro indicated that some target compounds showed good antibacterial activity against the tested plant

  设计、合成了一系列含有噻唑支架的类黄酮衍生物，并对其对立枯丝核菌、禾谷镰刀菌、禾谷镰刀菌、禾谷镰刀菌、立枯病菌、灰霉病菌和马里链格孢菌的抑制作用进行了评价。体外抗真菌生物测定结果表明，部分目标化合物对受试植物真菌表现出良好的抑菌活性，优于黄酮类天然产物槲皮素。引人注目的是，标题化合物6a、6b和6f对立枯丝核菌具有明显的抗真菌活性EC 50值分别为 9.6、35.5 和 21.5 μg/mL。化合物6b对禾本科革兰氏菌的EC 50值达到2.7 μg/mL。 图形概要
• Understanding the Cardioprotective Effects of Flavonols: Discovery of Relaxant Flavonols without Antioxidant Activity
  作者：Cheng Xue Qin、Xingqiang Chen、Richard A. Hughes、Spencer J. Williams、Owen L. Woodman

  DOI：10.1021/jm070352h

  日期：2008.3.1

  3 ',4 '-Dihydroxyflavonol (DiOHF) is a cardioprotective flavonol that can reduce injury after myocardial ischemia and reperfusion and thus is a promising small molecule for the treatment of cardiovascular disease. Like all vasoactive flavonols reported to date, DiOHF is both relaxant and antioxidant, hindering investigation of the relative contribution of each activity for the prevention of reperfusion injury. This study investigates structure-activity relationships of variations at the 3 ' and 4 ' positions of the B ring of DiOHF and vasorelaxant and antioxidant activities. Relaxation of rat isolated aortic rings precontracted with KCl revealed that the most active flavonols were those with a 4 '-hydroxyl group, with the opening of potassium channels as a possible contributing mechanism. For the antioxidant activity, with the exception of DiOHF, none of the flavonols investigated were able to significantly scavenge superoxide radical, and none of the three most potent vasorelaxant flavonols could prevent oxidant-induced endothelial dysfunction. The discovery of single-acting vasorelaxant flavonols without antioxidant activity, in particular 4 '-hydroxy-3 '-methoxyflavonol, will assist in investigating the mechanism of flavonol-induced cardioprotection.
• Pharmacophore model of the quercetin binding site of the SIRT6 protein
  作者：S. Ravichandran、N. Singh、D. Donnelly、M. Migliore、P. Johnson、C. Fishwick、B.T. Luke、B. Martin、S. Maudsley、S.D. Fugmann、R. Moaddel

  DOI：10.1016/j.jmgm.2014.01.004

  日期：2014.4

  SIRT6 is a histone deacetylase that has been proposed as a potential therapeutic target for metabolic disorders and the prevention of age-associated diseases. We have previously reported on the identification of quercetin and vitexin as SIRT6 inhibitors, and studied structurally related flavonoids including luteolin, kaempferol, apigenin and naringenin. It was determined that the SIRT6 protein remained active after immobilization and that a single frontal displacement could correctly predict the functional activity of the immobilized enzyme. The previous study generated a preliminary pharmacophore for the quercetin binding site on SIRT6, containing 3 hydrogen bond donors and one hydrogen bond acceptor. In this study, we have generated a refined pharmacophore with an additional twelve quercetin analogs. The resulting model had a positive linear behavior between the experimental elution time verses the fit values obtained from the model with a correlation coefficient of 0.8456. Published by Elsevier Inc.