7-hydroxy-8-methyl-2-phenyl-4H-benzofuro<3,2-g><1>benzopyran-4-one | 36747-88-3

• 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-8-methyl-2-phenyl-4H-benzofuro<3,2-g><1>benzopyran-4-one
• 英文别名: 7-hydroxy-8-methyl-2-phenyl-4H-chromen-4-one；7-hydroxy-8-methylflavone；7-hydroxy-8-methyl-2-phenyl-chromen-4-one；7-Hydroxy-8-methyl-2-phenyl-chromen-4-on；7-Hydroxy-8-methyl-flavon；7-Hydroxy-8-methyl-2-phenyl-4H-1-benzopyran-4-one；7-hydroxy-8-methyl-2-phenylchromen-4-one
• CAS: 36747-88-3
• 化学式: C₁₆H₁₂O₃
• 分子量: 252.269
• InChiKey: APZPBTFVVAFVHI-UHFFFAOYSA-N

物化性质

• 熔点：
  255-257 °C
• 沸点：
  466.5±45.0 °C(Predicted)
• 密度：
  1.300±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  19
• 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：
  3

反应信息

• 作为反应物：
  描述：

  7-hydroxy-8-methyl-2-phenyl-4H-benzofuro<3,2-g><1>benzopyran-4-one 在 potassium carbonate 作用下， 以 丙酮 为溶剂， 生成 6,7,8,9-tetrahydro-11-methyl-2-phenyl-4H-benzofuro<3,2-g><1>benzopyran-4-one
  参考文献：
  名称：

  Ahluwalia, V. K.; Adhikari, Raju; Singh, R. P., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1987, vol. 26, # 1-12, p. 229 - 231

  摘要：

  DOI：
• 作为产物：
  描述：

  7-羟基黄酮 在 氢溴酸 、 锌 作用下， 以 溶剂黄146 为溶剂， 反应 4.0h， 生成 7-hydroxy-8-methyl-2-phenyl-4H-benzofuro<3,2-g><1>benzopyran-4-one
  参考文献：
  名称：

  Jha, H. N.; Parmar, V. S.; Katyal, Mohan, Journal of the Indian Chemical Society, 1983, vol. 60, p. 411 - 412

  摘要：

  DOI：

文献信息

• Design, synthesis and evaluation of flavonoid derivatives as potential multifunctional acetylcholinesterase inhibitors against Alzheimer’s disease
  作者：Ren-Shi Li、Xiao-Bing Wang、Xiao-Jun Hu、Ling-Yi Kong

  DOI：10.1016/j.bmcl.2013.02.095

  日期：2013.5

  derivatives were designed, synthesized and evaluated as potential multifunctional AChE inhibitors against Alzheimer’s disease. Most of them exhibited potent AChE inhibitory activity, high selectivity for AChE over BuChE, and moderate to good inhibitory potency toward Aβ aggregation. Specifically, compound 12c was the strongest AChE inhibitor, being 20-fold more potent than galanthamine and twofold

  设计，合成和评估了一系列新的类黄酮衍生物，它们可作为对抗阿尔茨海默氏病的潜在多功能AChE抑制剂。他们中的大多数在丁酰胆碱酯酶表现出强大的乙酰胆碱酯酶抑制活性，高选择性乙酰胆碱酯酶，并适度向好的抑制能力β聚集。具体而言，化合物12C是最强的乙酰胆碱酯酶抑制剂，为20倍雪花胺更有效和双重比他克林更有效的，并且它也有能力抑制β聚集（接近参考化合物）并起金属螯合剂的作用。分子建模和酶动力学研究表明，它同时针对AChE的催化活性位点和外围阴离子位点。因此，应该对这类化合物进行彻底和系统的研究以治疗阿尔茨海默氏病。
• Palladium-catalyzed regioselective arylation of 7-hydroxyflavone with diaryliodonium salts
  作者：Yu-Ping Zhao、Jia-Lu Liao、Chen-Fu Liu

  DOI：10.1016/j.tetlet.2023.154573

  日期：2023.6

  A palladium-catalyzed regioselective arylation at the C6 position of 7-hydroxyflavone protocol was disclosed for the first time. The reaction occurs in carbamate directing group directed CH activation manner. The key to this high regioselectivity is the appropriate choice of carbamates as protecting/directing groups and H3PO4 additive in the presence of Pd (TFA)2 catalyst. Additionally, the procedure

  首次公开了钯催化的 7-羟基黄酮 C6 位区域选择性芳基化方案。该反应以氨基甲酸酯导向基团定向的CH活化方式发生。这种高区域选择性的关键是2存在下3PO4。此外，该程序为制备 6-芳基黄酮衍生物提供了一种权宜之计。
• Design and development of some thiazole-based flavanoids as novel antibacterial against pathogens causing surgical site infection for possible benefit in bone trauma via inhibition of DNA gyrase
  作者：Gang Zhao、Dengzhe Lan、Guobao Qi

  DOI：10.1111/cbdd.12999

  日期：2017.11

  In this study, a novel class of hybrid thiazole‐based flavanoid derivatives were synthesized and characterized by FT‐IR, 1H‐NMR, 13C‐NMR, mass and elemental analysis. These derivatives were evaluated for antibacterial activity for possible benefit in bone trauma via inhibition of DNA gyrase enzyme. Results suggested that compounds 9n, 9o, and 9p showed considerable inhibition of DNA gyrase with considerable activity against tested forty strains of Staphylococcus aureus clinical isolates. Moreover, compound 9n showed hydrogen bonding with LYS460 along with low binding free energy of −4.36 kcal/mol against DNA gyrase enzyme. The hemolytic activity of the potent compounds showed mild to no activity together with excellent pharmacokinetics, suggesting to have a potential for the development of designed compounds as novel antibacterial agents.
• Rangaswami; Seshadri, Proceedings - Indian Academy of Sciences, Section A, 1939, # 9, p. 7
  作者：Rangaswami、Seshadri

  DOI：——

  日期：——
• JHA, H. N.;PARMAR, V. S.;KATYAL, M., J. INDIAN CHEM. SOC., 1983, 60, N 4, 411-412
  作者：JHA, H. N.、PARMAR, V. S.、KATYAL, M.

  DOI：——

  日期：——