7,8-diacetoxy-3-phenylcoumarin | 857783-33-6

• 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: 7,8-diacetoxy-3-phenylcoumarin
• 英文别名: 7,8-Diacetoxy-3-phenyl-cumarin；(8-Acetyloxy-2-oxo-3-phenylchromen-7-yl) acetate；(8-acetyloxy-2-oxo-3-phenylchromen-7-yl) acetate
• CAS: 857783-33-6
• 化学式: C₁₉H₁₄O₆
• 分子量: 338.317
• InChiKey: MJMQPFPRJQOZQW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  25
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  78.9
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  7,8-diacetoxy-3-phenylcoumarin 在 盐酸 作用下， 以 甲醇 、 水 为溶剂， 反应 3.0h， 生成 7,8-dihydroxy-3-phenyl-2H-chromen-2-one
  参考文献：
  名称：

  Design and discovery of tyrosinase inhibitors based on a coumarin scaffold

  摘要：

  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。

  DOI：

  10.1039/c5ra14465e
• 作为产物：
  描述：

  sodium phenylacetate 、 alkaline earth salt of/the/ methylsulfuric acid 在 乙酸酐 作用下， 生成 7,8-diacetoxy-3-phenylcoumarin
  参考文献：
  名称：

  Bargellini, Gazzetta Chimica Italiana, 1927, vol. 57, p. 461

  摘要：

  DOI：

文献信息

• 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, antioxidant and antichagasic properties of a selected series of hydroxy-3-arylcoumarins
  作者：Natalia Robledo-O’Ryan、Maria João Matos、Saleta Vazquez-Rodriguez、Lourdes Santana、Eugenio Uriarte、Mauricio Moncada-Basualto、Francisco Mura、Michel Lapier、Juan Diego Maya、Claudio Olea-Azar

  DOI：10.1016/j.bmc.2016.11.033

  日期：2017.1

  disease). Interestingly, the current study revealed that small structural changes in the hydroxy-3-arylcoumarin core allow modulating both activities, suggesting that this scaffold has desirable properties for the development of promising classes of antichagasic compounds.

  氧化应激与查加斯（Chagas）等几种寄生虫病有关。能够选择性调节与疾病有关的生化过程的药物代表了有希望的多功能药物，可延缓或消除这种病理学进程。在当前的工作中，描述了不同取代的羟基-3-芳基香豆素，既发挥抗氧化剂活性又具有锥虫活性。在合成的化合物中，化合物8表现出最令人关注的特性，表现出对过氧自由基的适度清除能力（ORAC-FL = 2.23），并且对寄生克鲁维氏酵母的副鞭毛阶段具有高度选择性（IC 50 = 1.31μM），高于Nifurtimox（目前用于治疗南美锥虫病的药物）。有趣的是，当前的研究表明，羟基-3-芳基香豆素核心的细微结构变化允许调节这两种活性，这表明该支架对于开发有前途的抗chachagasic化合物具有理想的特性。
• Structure-Based Optimization of Coumarin hA₃ Adenosine Receptor Antagonists
  作者：Maria João Matos、Santiago Vilar、Saleta Vazquez-Rodriguez、Sonja Kachler、Karl-Norbert Klotz、Michela Buccioni、Giovanna Delogu、Lourdes Santana、Eugenio Uriarte、Fernanda Borges

  DOI：10.1021/acs.jmedchem.9b01572

  日期：2020.3.12

  Adenosine receptors participate in many physiological functions. Molecules that may selectively interact with one of the receptors are favorable multifunctional chemical entities to treat or decelerate the evolution of different diseases. 3-Arylcoumarins have already been studied as neuroprotective agents by our group. Here, differently 8-substituted 3-arylcoumarins are complementarily studied as ligands of adenosine receptors, performing radioligand binding assays. Among the synthesized compounds, selective A(3) receptor antagonists were found. 3-(4-Bromophenyl)-8-hydroxycoumarin (compound 4) displayed the highest potency and selectivity as A(3) receptor antagonist (K-i = 258 nM). An analysis of its X-ray diffraction provided detailed information on its structure. Further evaluation of a selected series of compounds indicated that it is the nature and position of the substituents that determine their activity and selectivity. Theoretical modeling calculations corroborate and explain the experimental data, suggesting this novel scaffold can be involved in the generation of candidates as multitarget drugs.
• Ghosh, Journal of the Chemical Society, 1916, vol. 109, p. 117
  作者：Ghosh

  DOI：——

  日期：——
• 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。