5-hydroxyfurano(4'',5''-6,7)flavone | 69367-25-5

• 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: 5-hydroxyfurano(4'',5''-6,7)flavone
• 英文别名: 5-hydroxyfurano(6,7-4'',5'')flavone；4-hydroxy-7-phenyl-furo[3,2-g]chromen-5-one；4-Hydroxy-7-phenylfuro[3,2-g]chromen-5-one
• CAS: 69367-25-5
• 化学式: C₁₇H₁₀O₄
• 分子量: 278.264
• InChiKey: YAFNUEQKAOXPIC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  21
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  59.7
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-hydroxyfurano(4'',5''-6,7)flavone 在 potassium carbonate 、 N,N-二乙基苯胺 作用下， 以 丙酮 为溶剂， 反应 26.0h， 生成 9-allyl-4-hydroxy-7-phenyl-5H-furo[3,2-g]chromen-5-one
  参考文献：
  名称：

  Design, synthesis and structure–activity relationship of novel semi-synthetic flavonoids as antiproliferative agents

  摘要：

  Various flavonoid scaffold based derivatives viz furochalcones (3a-e, 6a-d and 9a-d), furoflavones (10a-d, 11a-d,12a-d,18a&b), flavones (21a-d), furoaurones (13a,b,14a-d and 15a-d) and 7-styrylfurochromones (22a-d and 25a-e) were designed and synthesized. The novel compounds were evaluated for their anti-proliferative activity against a panel of 60 cancer cell lines comprising 9 types of tumors. Ten compounds belonging to the major subgroups of flavonoids viz furochalcones (3a, 3d, 6b, 9a and 9b), furoflavones (12a and 12c), furoaurones (15d), styrylfurochromones (25b and 25e) showed very promising activity. These active compounds were also evaluated in vitro as kinase inhibitors against CDK2/cyclin E1, CDK4/cyclin D1 and GSK-3 beta and the best inhibition was displayed against GSK-3 beta with the allylfurochalcone derivative 9b exhibiting 80% decrease in GSK-3 beta catalytic activity. On the other hand, the styrylfurochromone 25e interestingly showed a 13% enhancement of GSK-3 beta catalytic power and a 12% reduction in CDK4/cyclin D1 activity. Finally, the in vivo anti-tumor activity of 25e was evaluated against breast cancer induced in mice. The results showed a profound anti-tumor effect of 25e that accompanies a significant increase and decrease in the levels of GSK-3 beta and cyclin D1, respectively. (C) 2014 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2014.06.007
• 作为产物：
  描述：

  5H-呋喃并[3,2-g][1]苯并吡喃-5-酮,4-甲氧基-7-苯基- 在 氢溴酸 、 溶剂黄146 作用下， 反应 1.0h， 以90%的产率得到5-hydroxyfurano(4'',5''-6,7)flavone
  参考文献：
  名称：

  合成6-和9-烷基氨基甲基呋喃酮类黄酮作为胃保护剂。

  摘要：

  由天然存在的色酮，蚕豆素和k兰蛋白合成9-和6-烷基氨基甲基呋喃酮黄酮5a，b，9a-c，13a，b，15a-g和18。确定了这些化合物在乙醇损伤模型中的胃保护效力。结果表明，通过适当的取代，可以获得具有胃保护作用的呋喃黄酮。

  DOI：

  10.1016/j.ejmech.2007.01.019

文献信息

• Synthesis of 6- and 9-alkylaminomethyl furoflavones as gastroprotective agents
  作者：Fatma A. Ragab、Ghaneya S. Hassan、Hanan A. Yossef、Hanna A. Hashem

  DOI：10.1016/j.ejmech.2007.01.019

  日期：2007.8

  The synthesis of 9- and 6-alkylaminomethyl furoflavones 5a, b, 9a-c, 13a, b, 15a-g and 18 from the naturally occurring chromones visnagin and khellin. Gastroprotective potency of these compounds in the ethanol damage model was determined. The results indicate that, through appropriate substitution, furoflavones can be obtained that are gastroprotective.

  由天然存在的色酮，蚕豆素和k兰蛋白合成9-和6-烷基氨基甲基呋喃酮黄酮5a，b，9a-c，13a，b，15a-g和18。确定了这些化合物在乙醇损伤模型中的胃保护效力。结果表明，通过适当的取代，可以获得具有胃保护作用的呋喃黄酮。
• Pongaglabol, a new hydroxyfuranoflavone, and aurantiamide acetate, a dipeptide from the flowers of Pongamia glabra
  作者：Sunil K. Talapatra、Asok K. Mallik、Bani Talapatra

  DOI：10.1016/0031-9422(80)83083-4

  日期：1980.1

  Abstract Pongaglabol, a new hydroxyfuranoflavone, and aurantiamide acetate, a rarely occurring modified phenylalanine dipeptide, have been isolated together with 4 furanoflavones, karanjin, lancheolatin B, kanjone and pinnatin, a simple flavone, kanugin, a chromenoflavanone (−)-isolonchocarpin, two furanodiketones pongamol and ovalitenone, and β-sitosterol from the petrol and chloroform extracts of

  摘要 Pongaglabol，一种新的羟基呋喃黄酮，和醋酸金黄酮，一种很少出现的修饰苯丙氨酸二肽，与 4 种呋喃黄酮、karanjin、lancheolatin B、kanjone 和 pinnatin、简单的黄酮、kanugin、chromenoflavanone (-)-isolonchocar呋喃二酮 pongamol 和 ovalitenone，以及来自 Pongamia glabra 花的汽油和氯仿提取物中的 β-谷甾醇。根据光谱和化学证据，pongaglabol 的结构已确定为 5-羟基呋喃 (8,7-4",5") 黄酮。
• Scandium-Catalyzed Phenol-Directed Construction of 5-Carbonyl-4-hydroxybenzofurans via Intramolecular Friedel–Crafts Reaction
  作者：Takahito Kuribara、Ayahito Kaneki、Yuma Mihara、Honoka Yuba、Tetsuhiro Nemoto

  DOI：10.1021/acs.orglett.3c03123

  日期：2023.11.3

  5-carbonyl-4-hydroxybenzofurans via a phenol-directed intramolecular Friedel–Crafts reaction. This synthetic method was applied for the total synthesis of furanoflavones. Experimental studies and density functional theory calculations suggest that hydrogen bond interactions between the phenolic hydroxy group and the scandium complex realize regioselective intramolecular cyclization.

  在此，我们报道了通过苯酚引导的分子内弗里德尔-克来福特反应，钪催化的5-羰基-4-羟基苯并呋喃的区域选择性合成。该合成方法应用于呋喃黄酮的全合成。实验研究和密度泛函理论计算表明，酚羟基与钪配合物之间的氢键相互作用实现了区域选择性分子内环化。
• Talapatra, Bani; Mallik, Asok K.; Talapatra, Sunil K., Journal of the Indian Chemical Society, 1985, vol. 62, # 5, p. 408 - 409
  作者：Talapatra, Bani、Mallik, Asok K.、Talapatra, Sunil K.

  DOI：——

  日期：——
• HISHMAT O. H.; KHALIL K. M.; EL-EBRASHI N. M. A.; KHODEIR M. N. M., Z. NATURFORSCH., 1978, B 33, NO 12, 1491-1495
  作者：HISHMAT O. H.、 KHALIL K. M.、 EL-EBRASHI N. M. A.、 KHODEIR M. N. M.

  DOI：——

  日期：——