5-acetyl-6-allyloxy-4-methoxybenzofuran | 1000996-10-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并呋喃
• 英文名称: 5-acetyl-6-allyloxy-4-methoxybenzofuran
• 英文别名: O-allyl-visnaginone；1-[4-Methoxy-6-(2-propen-1-yloxy)-5-benzofuranyl]ethanone；1-(4-methoxy-6-prop-2-enoxy-1-benzofuran-5-yl)ethanone
• CAS: 1000996-10-0
• 化学式: C₁₄H₁₄O₄
• 分子量: 246.263
• InChiKey: QANAANYBMLULEX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.21
• 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：

  5-acetyl-6-allyloxy-4-methoxybenzofuran 在 selenium(IV) oxide 、 N,N-二乙基苯胺 、 sodium hydroxide 作用下， 以 乙醇 、 正丁醇 为溶剂， 反应 50.0h， 生成 3-(4-methoxy-5-oxo-7-phenyl-5H-furo[3,2-g]chromen-9-yl)acrylaldehyde
  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：

  齿阿米素 在 potassium carbonate 、 potassium hydroxide 作用下， 以 丙酮 为溶剂， 反应 25.0h， 生成 5-acetyl-6-allyloxy-4-methoxybenzofuran
  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

文献信息

• Synthesis and reactions of some new benzopyranone derivatives with potential biological activities
  作者：El-Sayed I. El-Desoky、Shar S. Al-Shihry

  DOI：10.1002/jhet.5570450648

  日期：2008.11

  to yield the ylidene nicotinonitrile and pyridone derivatives 4,7,10a-b. Reaction of 3 with aniline or aniline acting on multiple function X-H (X = NH, O, S) at its ortho position afforded the corresponding anils, imidazolylfurochromene and azepines compounds 11-17. On the other hand, oxidation of visnagin afforded chromene-6-carboxaldehyde derivative 18 which was condensed with different aryl or (heteroaryl)

  天然存在的化合物“ visnagine”衍生的visnaginone与烯丙基溴的反应生成了O-烯丙基visnaginone 1，对其进行了克莱森重排，生成了7-烯丙基苯并呋喃2衍生物。Vilsmeier Haack将2甲酰化可得到我们通用的起始化合物呋喃二烯-6-甲醛（3），将其与1,3-二酮环己烷，茚满二酮，丙二腈或氰基乙酸乙酯缩合，生成亚硝基烟腈和吡啶酮衍生物4,7,10a- b。3与苯胺或在其邻位作用于多功能XH（X = NH，O，S）的苯胺的反应位置得到相应的茴香，咪唑基呋喃酮和咪唑类化合物11-17。另一方面，通过氧化维斯那金，得到色烯-6-甲醛衍生物18，其与不同的芳基或（杂芳基）乙腈缩合，然后水解得到吡喃并[3,2 - g ]色烯-4,8-​​二酮衍生物20a- d和22。
• Synthesis and reactions of some new allyl furobenzopyranone derivatives
  作者：El-Sayed I. El-Desoky

  DOI：10.1002/jhet.5570440612

  日期：2007.11

  Reaction of visnaginone 1 with allyl bromide gave O-allyl visnaginone 2 which underwent Claisen rearrangement to yield 7-allylbenzofuran derivative 3. Reaction of 3 with different aromatic aldehydes gave the corresponding 5-cinnamoylbenzofuran derivatives 4a-d. Condensation of the latter chalcones 4a,c,d with hydrazine hydrate and phenylhydrazine provided, the corresponding pyrazoline derivatives 7a-f

  visnaginone 1与烯丙基溴的反应生成O-烯丙基visnaginone 2，将其进行克莱森重排，得到7-烯丙基苯并呋喃衍生物3。3与不同的芳族醛反应，得到相应的5-肉桂酰基苯并呋喃衍生物4a-d。提供的后一查耳酮4a，c，d与水合肼和苯肼缩合，得到相应的吡唑啉衍生物7a-f。化合物3与乙酸乙酯和碳酸二乙酯的克莱森缩合得到克莱森加合物8和12容易环化成9和13，并具有有趣的生物学特性。