8-hydroxy-3-phenylcoumarin | 6468-97-9

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 异黄酮类化合物
• 英文名称: 8-hydroxy-3-phenylcoumarin
• 英文别名: 8-Hydroxy-3-phenyl-2H-1-benzopyran-2-one；8-hydroxy-3-phenylchromen-2-one
• CAS: 6468-97-9
• 化学式: C₁₅H₁₀O₃
• 分子量: 238.243
• InChiKey: URQVILQIFIJNLS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  18
• 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：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  8-hydroxy-3-phenylcoumarin 、 乙酸酐 在 吡啶 作用下， 生成 8-acetoxy-3-phenylcoumarin
  参考文献：
  名称：

  Richtzenhain; Alfredsson, Acta Chemica Scandinavica (1947), 1953, vol. 7, p. 1173,1176

  摘要：

  DOI：
• 作为产物：
  描述：

  sodium phenylacetate 在 氢碘酸 、 乙酸酐 作用下， 生成 8-hydroxy-3-phenylcoumarin
  参考文献：
  名称：

  Richtzenhain; Alfredsson, Acta Chemica Scandinavica (1947), 1953, vol. 7, p. 1173,1176

  摘要：

  DOI：

文献信息

• Design and discovery of tyrosinase inhibitors based on a coumarin scaffold
  作者：M. J. Matos、C. Varela、S. Vilar、G. Hripcsak、F. Borges、L. Santana、E. Uriarte、A. Fais、A. Di Petrillo、F. Pintus、B. Era

  DOI：10.1039/c5ra14465e

  日期：——

  A novel series of 3-aryl and 3-heteroarylcoumarins displaying tyrosinase inhibitory activity.

  一部包含对酪氨酸酶抑制活性的3-芳基和3-杂环基香豆素的小说系列。
• Antibacterial Activity and Molecular Docking Studies of a Selected Series of Hydroxy-3-arylcoumarins
  作者：Pisano、Kumar、Medda、Gatto、Pal、Fais、Era、Cosentino、Uriarte、Santana、Pintus、Matos

  DOI：10.3390/molecules24152815

  日期：——

  Antibiotic resistance is one of the main public health concerns of this century. This resistance is also associated with oxidative stress, which could contribute to the selection of resistant bacterial strains. Bearing this in mind, and considering that flavonoid compounds are well known for displaying both activities, we investigated a series of hydroxy-3-arylcoumarins with structural features of flavonoids for their antibacterial activity against different bacterial strains. Active compounds showed selectivity against the studied Gram-positive bacteria compared to Gram-negative bacteria. 5,7-Dihydroxy-3-phenylcoumarin (compound 8) displayed the best antibacterial activity against Staphylococcus aureus and Bacillus cereus with minimum inhibitory concentrations (MICs) of 11 g/mL, followed by Staphylococcus aureus (MRSA strain) and Listeria monocytogenes with MICs of 22 and 44 g/mL, respectively. Moreover, molecular docking studies performed on the most active compounds against Staphylococcus aureus tyrosyl-tRNA synthetase and topoisomerase II DNA gyrase revealed the potential binding mode of the ligands to the site of the appropriate targets. Preliminary structure–activity relationship studies showed that the antibacterial activity can be modulated by the presence of the 3-phenyl ring and by the position of the hydroxyl groups at the coumarin scaffold.

  抗生素耐药性是本世纪主要的公共卫生关注点之一。这种耐药性也与氧化应激有关，可能有助于选择耐药性细菌菌株。考虑到这一点，并且考虑到黄酮类化合物以展示这两种活性而闻名，我们研究了一系列具有黄酮类结构特征的羟基-3-芳基香豆素对不同细菌菌株的抗菌活性。活性化合物对所研究的革兰氏阳性细菌表现出了选择性，而不同于革兰氏阴性细菌。5,7-二羟基-3-苯基香豆素（化合物8）对金黄色葡萄球菌和蜡样芽孢杆菌显示出最佳的抗菌活性，最小抑制浓度（MICs）分别为11 g/mL，其次是金黄色葡萄球菌（MRSA菌株）和李斯特菌属，MICs分别为22和44 g/mL。此外，对金黄色葡萄球菌酪氨酰-tRNA合成酶和DNA旋转酶II的最活性化合物进行的分子对接研究揭示了配体与适当靶点位点的潜在结合方式。初步的结构-活性关系研究显示，3-苯基环的存在和香豆素骨架上羟基团的位置可以调节抗菌活性。
• Synthesis and biological evaluation of 3-arylcoumarins as potential anti-Alzheimer's disease agents
  作者：Jie Yang、Pingping Zhang、Yuheng Hu、Teng Liu、Jie Sun、Xiaojing Wang

  DOI：10.1080/14756366.2019.1574297

  日期：2019.1.1

  the extremely complex pathogenesis. Accumulating evidence indicates there is a close relationship between several enzymes and Alzheimer's disease. Various substituted 3-arylcoumarin derivatives were synthesised, and their in vitro activity, including cholinesterase inhibitory activity, monoamine oxidase inhibitory activity, and antioxidant activity were investigated. Most of the compounds exhibited

  抽象的 阿尔茨海默氏病是一种神经退行性疾病，其发病机理极为复杂。越来越多的证据表明，几种酶与阿尔茨海默氏病之间存在密切的关系。合成了各种取代的3-芳基香豆素衍生物，并研究了它们的体外活性，包括胆碱酯酶抑制活性，单胺氧化酶抑制活性和抗氧化活性。大多数化合物表现出高活性。因此3-芳基香豆素类化合物具有治疗阿尔茨海默氏病的潜力。
• Study of Coumarin-Resveratrol Hybrids as Potent Antioxidant Compounds
  作者：Maria Matos、Francisco Mura、Saleta Vazquez-Rodriguez、Fernanda Borges、Lourdes Santana、Eugenio Uriarte、Claudio Olea-Azar

  DOI：10.3390/molecules20023290

  日期：——

  In the present work we synthesized a selected series of hydroxylated 3-phenylcoumarins 5–8, with the aim of evaluating in detail their antioxidant properties. From an in depth study of the antioxidant capacity data (ORAC-FL, ESR, CV and ROS inhibition) it was concluded that these derivatives are very good antioxidants, with very interesting profiles in all the performed assays. The study of the effect of the number and position of the hydroxyl groups on the antioxidant activity was the principal aim of this study. In particular, 7-hydroxy-3-(3'-hydroxy)phenylcoumarin (8) proved to be the most active and effective antioxidant of the selected series in four of the performed assays (ORAC-FL = 11.8, capacity of scavenging hydroxyl radicals = 54%, Trolox index = 2.33 and AI30 index = 0.18). However, the presence of two hydroxyl groups on this molecule did not increase greatly the activity profile. Theoretical evaluation of ADME properties of all the derivatives was also carried out. All the compounds can act as potential candidates for preventing or minimizing the free radical overproduction in oxidative-stress related diseases. These preliminary findings encourage us to perform a future structural optimization of this family of compounds.

  在本研究中，我们合成了一系列选择性的羟基化3-苯基香豆素5-8，旨在详细评估其抗氧化特性。通过对抗氧化能力数据（ORAC-FL、ESR、CV和ROS抑制）的深入研究，我们得出结论，这些衍生物是非常好的抗氧化剂，在所有进行的实验中表现出非常有趣的特征。研究羟基数量和位置对抗氧化活性的影响是本研究的主要目标。特别是，7-羟基-3-(3'-羟基)苯基香豆素（8）被证明是所选系列中在四项实验中最活跃和有效的抗氧化剂（ORAC-FL=11.8，羟基自由基清除能力=54%，Trolox指数=2.33，AI30指数=0.18）。然而，这种分子上两个羟基的存在并没有显著提高活性特征。还对所有衍生物的ADME特性进行了理论评估。所有化合物都可以作为潜在候选者，以防止或减少与氧化应激相关疾病中自由基的过量产生。这些初步发现鼓励我们对这一类化合物进行未来的结构优化。
• Synthesis and biological evaluation of 3-arylcoumarin derivatives as potential anti-diabetic agents
  作者：Yuheng Hu、Bing Wang、Jie Yang、Teng Liu、Jie Sun、Xiaojing Wang

  DOI：10.1080/14756366.2018.1518958

  日期：2019.1.1

  Abstract A variety of substituted 3-arylcoumarin derivatives were synthesised through microwave radiation heating. The method has characteristics of environmental friendliness, economy, simple separation, and purification process, less by-products and high reaction yield. Those 3-arylcoumarin derivatives were screened for antioxidant, α-glucosidase inhibitory and advanced glycation end-products (AGEs)

  抽象的 通过微波辐射加热合成了多种取代的3-芳基香豆素衍生物。该方法具有环境友好，经济，分离纯化工艺简单，副产物少，反应收率高的特点。筛选了那些3-芳基香豆素衍生物的抗氧化剂，α-葡萄糖苷酶抑制物和晚期糖基化终产物（AGEs）形成抑制物。大多数化合物表现出显着的抗氧化剂和AGEs形成抑制活性。抗糖尿病活性研究表明，化合物11和17在体内与标准药物glibenclamide等效。根据实验结果，目标化合物35可用作开发抗糖尿病新药的先导化合物。整个实验表明，抗糖尿病活性在3-芳基香豆素中普遍存在，为抗糖尿病活性药物的开发增加了新的天然骨架。