7-hydroxy-4-oxo-2-phenyl-4H-chromene-8-carbaldehyde | 42345-25-5

• 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: 7-hydroxy-4-oxo-2-phenyl-4H-chromene-8-carbaldehyde
• 英文别名: 8-Formyl-7-hydroxyflavon；4h-1-Benzopyran-8-carbaldehyde,7-hydroxy-4-oxo-2-phenyl-；7-hydroxy-4-oxo-2-phenylchromene-8-carbaldehyde
• CAS: 42345-25-5
• 化学式: C₁₆H₁₀O₄
• 分子量: 266.253
• InChiKey: SVQJSYOXXVCFTA-UHFFFAOYSA-N

物化性质

• 熔点：
  223-224 °C
• 沸点：
  476.9±45.0 °C(Predicted)
• 密度：
  1.405±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• 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-4-oxo-2-phenyl-4H-chromene-8-carbaldehyde 在 potassium carbonate 、 三乙胺 作用下， 以 乙醇 、 丙酮 为溶剂， 反应 5.0h， 生成 (2E)-N-(3-chlorobenzyl)-2-cyano-3-(7-methoxy-4-oxo-2-phenyl-4H-chromen-8-yl)acrylamide
  参考文献：
  名称：

  Synthesis and biological evaluation of flavone-8-acrylamide derivatives as potential multi-target-directed anti Alzheimer agents and investigation of binding mechanism with acetylcholinesterase

  摘要：

  In a search for novel multifunctional anti-Alzheimer agents, a congeneric set of seventeen flavone-8-acrylamide derivatives (8a-q) were synthesized and evaluated for their cholinesterase inhibitory, antioxidant, neuroprotective and modulation of A beta aggregation activities. The target compounds showed effective and selective inhibitory activity against the AChE over BuChE. In addition, the target compounds also showed moderate antioxidant activity and strong neuroprotective capacities, and accelerated dosage-dependently the A beta aggregation. Also, we presented here a complete study on the interaction of 8a, 8d, 8e, 8h and 8i with AChE. Through fluorescence emission studies, the binding sites number found to be 1, binding constants were calculated as 2.04 x 10(4), 2.22 x 10(4), 1.18 x 10(4), 9.8 x 10(3) and 3.2 x 10(4) M-1 and free energy change as -5.83, -5.91, -5.51, -5.41 and -6.12 kcal M-1 at 25 degrees C which were well agreed with the computational calculations indicating a strong binding affinity of flavones and AChE. Furthermore, the CD studies revealed that the secondary structure of AChE became partly unfolded upon binding with 8a, 8d, 8e, 8h and 8i.

  DOI：

  10.1016/j.bioorg.2019.102960
• 作为产物：
  描述：

  2,4-二羟基苯乙酮 在 乌洛托品 、 potassium carbonate 作用下， 以 丙酮 为溶剂， 反应 20.0h， 生成 7-hydroxy-4-oxo-2-phenyl-4H-chromene-8-carbaldehyde
  参考文献：
  名称：

  新型取代吡喃环合黄酮的合成

  摘要：

  已经开发了一种简单有效的一锅法，用于合成一些新的功能化吡喃并稠合的黄酮衍生物，即烷基4,8-二氧-2--2-苯基-4,8-​​二氢吡喃[2,3 - f ]亚甲基-10-羧酸酯和在三苯基存在下使用二烷基乙炔二羧酸酯从7-羟基黄酮和7-羟基8-甲酰基黄酮中合成4-氧代-2-苯基-4-苯基-4,8-​​二氢吡喃[2,3- f ] 1，2-二甲基吡喃酮[ 8,9-二羧酸]膦。通过FT-IR，1 H和13 C NMR和质谱分析阐明了所有合成化合物的结构。

  DOI：

  10.1134/s1070363216050248

文献信息

• Construction of Highly Functionalized Xanthones via Rh-Catalyzed Cascade C–H Activation/<i>O</i>-Annulation
  作者：Sagar D. Nale、Debabrata Maiti、Yong Rok Lee

  DOI：10.1021/acs.orglett.1c00391

  日期：2021.4.2

  facile and efficient strategy for obtaining functionalized and multihydroxylated xanthones via Rh catalysis under redox-neutral conditions is developed. Diverse salicylaldehydes bearing heterocycles, aromatics, and fused aromatics can be rapidly coupled with 1,4-benzoquinones or 1,4-hydroquinones to afford valuable xanthones via cascade C–H/O–H functionalization and annulation. This protocol provides a

  开发了一种在氧化还原中性条件下通过Rh催化获得官能化的和多羟基化的氧杂蒽的简便有效的策略。带有杂环，芳族化合物和稠合芳族化合物的不同水杨醛可以与1，4-苯醌或1,4-氢醌快速偶联，通过级联的C–H / O–H功能化和环化反应提供有价值的氧杂蒽。该协议提供了一种通过后期功能化获得生物活性物质的快速合成方法，并可以制备天然产物，例如次烯脂烯酮，普尼弗洛酮N和鸦胆素。
• Single and double intramolecular proton transfers in the electronically excited state of flavone derivatives
  作者：I. E. Serdiuk、A. D. Roshal

  DOI：10.1039/c5ra13912k

  日期：——

  to take part in Excited State Intramolecular Double Proton Transfer (ESIDPT), we synthesized two carbonyl derivatives of 3,7-dihydroxyflavone, both containing two different proton-transfer sites as well as related carbonyl derivatives of 3-hydroxyflavone and 7-hydroxyflavone. All the examined hydroxyflavones were found to participate in the Excited State Intramolecular Proton Transfer (ESIPT). ESIPT

  为了创建能够参与激发态分子内双质子转移（ESIDPT）的黄酮衍生物，我们合成了3,7-二羟基黄酮的两个羰基衍生物，它们都包含两个不同的质子转移位点以及相关的3-羟基黄酮和7-羟基黄酮。发现所有检查的羟基黄酮均参与兴奋态分子内质子转移（ESIPT）。与涉及7-羟基和6 / 8-羰基片段的ESIPT相比，涉及3-羟基和4-羰基的ESIPT具有更高的阻隔性。根据提供的数据，3,7-二羟基-2-苯基-6-（3-苯基丙酰基）-4 H-chromen-4-one经历两阶段的ESIDPT，形成中间互变异构体。这种ESIDPT会导致互变异构形式，其激发态的辐射失活速率异常低，从而限制了低荧光量子产率。3,7-二羟基-4-氧代-2-苯基-4 H-亚甲基-8-甲醛在电子激发态下的行为类似于3-羟基黄酮衍生物，因此我们推断该化合物中存在单个ESIPT 。
• Synthesis and biological evaluation of novel flavone/triazole/benzimidazole hybrids and flavone/isoxazole-annulated heterocycles as antiproliferative and antimycobacterial agents
  作者：Yerrabelly Jayaprakash Rao、Thummala Sowjanya、Gogula Thirupathi、Nandula Yadagiri Sreenivasa Murthy、Sudha Sravanti Kotapalli

  DOI：10.1007/s11030-018-9833-4

  日期：2018.11

  AbstractA series of new flavone/isoxazole fused heterocycles 5a–f and flavone/1,2,3-triazole/benzimidazole hybrid heterocycles compounds 7a–t were synthesized via an intramolecular cyclization and Cu(I)-catalyzed click 1,3-dipolar cycloaddition. The products were evaluated for their antiproliferative activity against human breast cancer cell line (MCF-7) using sulforhodamine B assay (SRB) and antimycobacterial

  摘要通过分子内环化和Cu（I）催化的点击1,3-偶极环加成反应合成了一系列新的黄酮/异恶唑稠合杂环5a-f和黄酮/ 1,2,3-三唑/苯并咪唑杂合杂环化合物7a-t。使用磺基罗丹明B测定（SRB）评估了产品对人乳腺癌细胞系（MCF-7）的抗增殖活性，并使用浊度测定法评估了产品的抗分枝杆菌活性。大多数测试化合物显示出抗增殖活性和抗分枝杆菌活性。化合物7l，7q和7r显示出中等的抗增殖活性，IC50值为 17.9、14.2、19.1（\ upmu \ hbox M} \）分别地，化合物5a和化合物5a在30 （\ upmu \ hbox M} \）浓度下显示出中等的抗分枝杆菌活性，抑制率为41.7％  。 图形概要
• A tandem synthesis of 3-aroylcoumarinoflavones catalyzed by l-proline and their antioxidant activity
  作者：G. Thirupathi、E. Yadaiah Goud、Y. Hemasri、MD. Suban Ali、Y. Jayaprakash Rao

  DOI：10.1007/s13738-016-0995-7

  日期：2017.2

  efficient and high-yielding synthesis of 3-aroylcoumarinoflavones has been developed by the condensation of easily synthesized 7-hydroxy-8-formylflavones and benzoyl acetonitriles in the presence of catalytic amount of l-proline in ethanol reflux. All the synthesized compounds were evaluated for their antioxidant activity. Some of the compounds showed very good activity compared to standard BHT.

  通过在乙醇回流中催化量的1-脯氨酸的存在下，通过容易合成的7-羟基-8-甲酰基黄酮与苯甲酰基乙腈的缩合，已经开发了一种容易，方便，有效且高产的3-芳酰基香豆素黄酮合成方法。评价所有合成的化合物的抗氧化活性。与标准BHT相比，某些化合物显示出非常好的活性。
• Synthesis of 3-Aroylcoumarin-Flavone Hybrids
  作者：Hulluru S.P. Rao、Venkata S. Tangeti

  DOI：10.2174/157017812800167501

  日期：2012.3.1

  A facile two step synthesis of 3-aroylcoumarin-flavone hybrids was achieved from 7-hydroxyflavone and α- oxoketene dithioacetals. In the first step 7-hydroxyflavone was regioselectively formylated under Duff reaction conditions. Resulting 8-formyl-7-hydroxy flavones were condensed with α-oxoketene dithioacetals in the presence of a catalytic amount of piperidine to furnish 3-aroylcoumarin-flavone hybrids.

  一种简单的两步合成方法成功合成了3-芳酰香豆素-黄酮杂化物，反应物为7-羟基黄酮和α-氧代酮二硫代乙酰材料。在第一步中，7-羟基黄酮在Duff反应条件下进行了区域选择性醛化。生成的8-醛-7-羟基黄酮与α-氧代酮二硫代乙酰材料在催化量哌啶的存在下进行缩合，得到3-芳酰香豆素-黄酮杂化物。