5H-呋喃并[3,2-g][1]苯并吡喃-5-酮,4-甲氧基-7-苯基- | 1232-43-5

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 黄酮类化合物
• 中文名称: 5H-呋喃并[3,2-g][1]苯并吡喃-5-酮,4-甲氧基-7-苯基-
• 中文别名: 5H-呋喃并[3,2-g][1]苯并吡喃-5-酮,4-甲氧基-7-苯基-
• 英文名称: pinnatin
• 英文别名: 4-methoxy-7-phenyl-5H-furo[3,2-g]chromen-5-one；4-methoxy-7-phenyl-furo[3,2-g]chromen-5-one；4-Methoxy-7-phenyl-furo[3,2-g]chromen-5-on；4-methoxy-7-phenylfuro[3,2-g]chromen-5-one
• CAS: 1232-43-5
• 化学式: C₁₈H₁₂O₄
• 分子量: 292.291
• InChiKey: QNWOJWLIFBMWKQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  48.7
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5H-呋喃并[3,2-g][1]苯并吡喃-5-酮,4-甲氧基-7-苯基- 在 potassium dichromate 、 硫酸 作用下， 生成 7-hydroxy-5-methoxy-4-oxo-2-phenyl-4H-chromene-6-carbaldehyde
  参考文献：
  名称：

  某些取代的呋喃色酮，苯并呋喃和黄酮衍生物的合成和抗惊厥活性。

  摘要：

  合成了呋喃色酮，2-苯基色酮（黄酮）和被硫代氨基脲或噻唑烷丁-4-酮取代的苯并呋喃衍生物。分别以丙戊酸和苯妥英钠为参考标准，对所有新合成的化合物在皮下戊四氮诱发的癫痫发作（scPTZ）和最大电击诱发的癫痫发作（MES）试验中均进行了抗惊厥活性的测试。scPTZ模型中活性最高的化合物为1c，2b，5a和7e，在腹膜内给药时在300 mg / kg时显示出100％的保护作用。此外，研究了三种活性最高的化合物（1c，2b，5a）的预处理对小鼠4-氨基吡啶诱导的致死性的影响。用这些化合物进行预处理显着增加了阵挛性和强直性惊厥的潜伏期，并防止了4-氨基吡啶诱发的死亡。因此，这提供了这些化合物的抗惊厥活性和对它们的神经保护活性的证据。基于获得的数据研究了构效关系。

  DOI：

  10.1248/cpb.58.1148
• 作为产物：
  描述：

  4-allyloxy-2-hydroxy-3-iodo-6-methoxyacetophenone 在 氢氧化钾 、 四氧化锇 、 potassium metaperiodate 、 硫酸 、 N,N-二甲基苯胺 作用下， 以 吡啶 、 乙醇 为溶剂， 反应 7.25h， 生成 5H-呋喃并[3,2-g][1]苯并吡喃-5-酮,4-甲氧基-7-苯基-
  参考文献：
  名称：

  Ahluwalia, V. K.; Prakash, Chandra; Mehta, Kamal Deep, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1980, vol. 19, # 12, p. 1081 - 1082

  摘要：

  DOI：

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。
• Furo-chromones and -Coumarins. XII. Synthesis of Fraxinol from Bergapten and of Baicalein from Visnagin
  作者：Alexander Schönberg、Nasry Badran、Nicolas A. Starkowsky

  DOI：10.1021/ja01625a055

  日期：1955.10
• Design, synthesis and structure–activity relationship of novel semi-synthetic flavonoids as antiproliferative agents
  作者：F.A. Ragab、T.A.A. Yahya、M.M. El-Naa、R.K. Arafa

  DOI：10.1016/j.ejmech.2014.06.007

  日期：2014.7

  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.
• Micky; Saleh; Mohamed, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2006, vol. 45, # 6, p. 1579 - 1583
  作者：Micky、Saleh、Mohamed、Mohamed、Salem

  DOI：——

  日期：——