7-hydroxy-2-phenyl-3-benzoylchromone | 117096-61-4

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 高异黄酮
• 英文名称: 7-hydroxy-2-phenyl-3-benzoylchromone
• 英文别名: 3-benzoyl-7-hydroxyflavone；3-benzoyl-7-hydroxy-2-phenyl-chromen-4-one；3-Benzoyl-7-hydroxy-2-phenyl-chromen-4-on；7-Hydroxy-3-benzoyl-flavon；3-benzoyl-7-hydroxy-2-phenyl-4H-chromen-4-one；3-benzoyl-7-hydroxy-2-phenylchromen-4-one
• CAS: 117096-61-4
• 化学式: C₂₂H₁₄O₄
• 分子量: 342.351
• InChiKey: STHYGAWWAZVJAY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  26
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  63.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  7-hydroxy-2-phenyl-3-benzoylchromone 在 potassium carbonate 作用下， 生成 7-羟基黄酮
  参考文献：
  名称：

  氧杂环的合成

  摘要：

  已经开发出一种合成3-酮-γ-吡喃酮中间体的黄酮，黄酮和色酮的通用方案。已经概述了使用类似方法方便地合成其他氧杂环的方法。

  DOI：

  10.1016/j.tetlet.2005.12.062
• 作为产物：
  描述：

  3-benzoyl-7-benzoyloxy-2-phenyl-chromen-4-one 在 硫酸 作用下， 生成 7-hydroxy-2-phenyl-3-benzoylchromone
  参考文献：
  名称：

  Trivedi et al., Journal of the Indian Chemical Society, 1943, vol. 20, p. 171

  摘要：

  DOI：

文献信息

• Synthesis and properties of 3-acyl-γ-pyrones, a novel class of flavones and chromones
  作者：A.K. Ganguly、S. Kaur、P.K. Mahata、D. Biswas、B.N. Pramanik、T.M. Chan

  DOI：10.1016/j.tetlet.2005.04.010

  日期：2005.6

  Using modified Baker–Venkataraman reaction a novel class of 3-acyl flavones and chromones have been synthesised. Reaction mechanism for their formation have been elucidated. The properties of 3-acyl flavonoids indicate them to be precursors for the synthesis of flavones.

  使用改良的Baker-Venkataraman反应，可以合成一类新型的3-酰基黄酮和色酮。已经阐明了其形成的反应机理。3-酰基类黄酮的性质表明它们是黄酮合成的前体。
• Flavones. 2. Synthesis and structure-activity relationship of flavodilol and its analogs. A novel class of antihypertensive agents with catecholamine depleting properties
  作者：E. S. C. Wu、T. E. Cole、T. A. Davidson、M. A. Dailey、K. G. Doring、M. Fedorchuk、J. T. Loch、T. L. Thomas、J. C. Blosser

  DOI：10.1021/jm00121a034

  日期：1989.1

  (3-Phenyl-7-flavonoxy)propanolamines have been shown to exhibit antihypertensive activity in spontaneously hypertensive rats. Although they are structurally similar to classical beta-adrenergic blocking compounds, their activity is not due to inhibition of beta-adrenoceptors. In the present study, a series of simple flavonoxypropanolamines was prepared to further explore the structural requirements for the antihypertensive effect of these compounds. A structure-activity relationship of these derivatives indicates that the position of the oxypropanolamine side chain, the hydroxy group of the side chain, steric bulkiness and length of N substituents, degree of the N-substitution, phenyl group at the 2-position of the chromone nucleus, and substituents of the phenyl group or B ring of the flavone play significant roles in imparting pharmacological effects. In addition, there is a good correlation between the antihypertensive activity and depletion of myocardial norepinephrine. Of these analogues tested, the most effective one was flavodilol. Only the 8-substituted analogue 6 was found to be a beta-antagonist. Flavodilol was chosen for in-depth pharmacological, toxicological, and clinical evaluation.

  含有(3-苯基-7-黄酮氧基)丙醇胺结构的化合物已被证明在自发性高血压大鼠中表现出抗高血压活性。尽管它们在结构上与经典的β-肾上腺素能阻断剂类似，但其活性并非由于β-肾上腺素受体的抑制。在本研究中，制备了一系列简单的黄酮氧基丙醇胺衍生物，以进一步探索这些化合物抗高血压效应的结构要求。这些衍生物的结构-活性关系研究表明，氧基丙醇胺侧链的位置、侧链上的羟基、N-取代基的立体位阻和长度、N取代的程度、色原核2位上的苯基基团，以及黄酮苯基或B环上的取代基在赋予药理效应方面起着重要作用。此外，抗高血压活性与心肌去甲肾上腺素的耗竭之间存在良好的相关性。在所有测试的类似物中，最有效的化合物是flavodilol。只有8-取代类似物6被发现是β-受体拮抗剂。Flavodilol被选中进行深入的药理学、毒理学和临床评估。
• Synthesis, Topoisomerase I Inhibitory and Cytotoxic Activities of Chromone Derivatives
  作者：Chirattikan Maicheen、Jiraphun Jittikoon、Opa Vajragupta、Jiraporn Ungwitayatorn

  DOI：10.2174/1573406411309030003

  日期：2013.2.1

  A series of chromone derivatives were designed as potential topoisomerase I (Top I) inhibitors based on the docking simulation study. Sixteen synthesized compounds were evaluated for Top I inhibitory activity and some compounds were further tested for in vitro cytotoxic activity. The most potent inhibitor, chromone 11b showed greater inhibitory activity (IC50 = 1.46 μM) than the known Top I inhibitors, i.e., camptothecin, fisetin and morin, but inactive against breast cancer cell (MCF-7), oral cavity cancer cell (KB) and small cell lung cancer (NCI-H187). Chromone 11c, another potent inhibitor (IC50 = 6.16 μM), exhibited cytotoxic activity against KB (IC50 = 73.32 μM) and NCI-H187 (IC50 = 36.79 μM).

  根据对接模拟研究，设计了一系列铬酮衍生物作为潜在的拓扑异构酶 I（Top I）抑制剂。对合成的 16 个化合物进行了拓扑异构酶 I 抑制活性评估，并进一步对一些化合物进行了体外细胞毒性测试。最有效的抑制剂色酮 11b 比已知的 Top I 抑制剂喜树碱、鱼藤素和吗啉具有更强的抑制活性（IC50 = 1.46 μM），但对乳腺癌细胞（MCF-7）、口腔癌细胞（KB）和小细胞肺癌（NCI-H187）没有活性。Chromone 11c 是另一种强效抑制剂（IC50 = 6.16 μM），对 KB（IC50 = 73.32 μM）和 NCI-H187 （IC50 = 36.79 μM）具有细胞毒性活性。
• New Syntheses of 3-Aroylflavone Derivatives; Knoevenagel Condensation and Oxidation versus One-Pot Synthesis
  作者：Diana Pinto、Artur Silva、Patrícia Vaz、Djenisa Rocha、José Cavaleiro

  DOI：10.1055/s-0032-1317159

  日期：——

  syntheses of 3-aroylflavones have been established. In the first synthesis the use of microwave irradiation led to an improvement in the yields of both the Knoevenagel condensation of β-diketones with aldehydes to afford 3-aroylflavanones and of their oxidation to 3-aroylflavones. In the second and more general synthesis, a novel and efficient procedure for 3-aroylflavones involves a one-pot reaction between

  已经建立了 3-芳酰基黄酮的两种合成方法。在第一次合成中，微波辐射的使用导致 β-二酮与醛的 Knoevenagel 缩合得到 3-芳酰基黄烷酮以及它们氧化为 3-芳酰基黄酮的产率的提高。在第二个和更一般的合成中，3-芳酰基黄酮的新型有效程序涉及在双（三甲基甲硅烷基）氨基锂存在下 2'-羟基苯乙酮和芳酰氯之间的一锅反应。
• An efficient one-pot synthesis of flavones
  作者：Chin Fei Chee、Michael J.C. Buckle、Noorsaadah Abd. Rahman

  DOI：10.1016/j.tetlet.2011.04.022

  日期：2011.6

  Flavones were prepared using a one-pot procedure starting from the corresponding 2'-hydroxyacetophenones. The latter were treated with 3 equiv of aroyl chloride in wet K2CO3/acetone (1% w/w water) to afford a good yield of flavone and a smaller amount of 3-aroylflavone. Evidence was obtained that the reaction proceeds via a triketone intermediate. When the reactants were heated in 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) and pyridine, the 3-aroylflavone was obtained exclusively. Use of a stoichiometric amount of aroyl chloride afforded only the corresponding flavone. (C) 2011 Elsevier Ltd. All rights reserved.