1-(7-bromo-6-hydroxy-4-methoxy-1-benzofuran-5-yl)-3-(4-chlorophenyl)prop-2-en-1-one | 1350717-55-3

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: 1-(7-bromo-6-hydroxy-4-methoxy-1-benzofuran-5-yl)-3-(4-chlorophenyl)prop-2-en-1-one
• CAS: 1350717-55-3
• 化学式: C₁₈H₁₂BrClO₄
• 分子量: 407.648
• InChiKey: AEVXTPKABZQXGG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.46
• 重原子数：
  24.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  59.67
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  1-(7-bromo-6-hydroxy-4-methoxy-1-benzofuran-5-yl)-3-(4-chlorophenyl)prop-2-en-1-one 在 selenium(IV) oxide 作用下， 以 正丁醇 为溶剂， 反应 24.0h， 以63%的产率得到9-bromo-7-(4-chlorophenyl)-4-methoxy-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：

  9-bromovisnagin 在 potassium hydroxide 、 sodium hydroxide 作用下， 以 乙醇 为溶剂， 反应 25.0h， 生成 1-(7-bromo-6-hydroxy-4-methoxy-1-benzofuran-5-yl)-3-(4-chlorophenyl)prop-2-en-1-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

文献信息

• DNA binding, antiviral activities and cytotoxicity of new furochromone and benzofuran derivatives
  作者：Omaima Mohamed Abdelhafez、Nehad Ahmed Abedelatif、Farid A. Badria

  DOI：10.1007/s12272-011-1006-2

  日期：2011.10

  which on amidation using morpholine, a sulonamido derivative (7) was obtained. Alkaline hydrolysis of the latter compound yielded 7-N-morpholinosulsamidobenzofuran (8) which was condensed with some aromatic aldehydes to yield the corresponding chalcone compounds (9a–e). Demethylation of visnagin afforded norvisnagin (10). The reaction of 10 with ethylbromoacetate in dry acetone yielded the ester benzopyran

  visnagin (1) 的溴化得到 9-bromovisnagin (2)，其碱性水解得到 3-乙酰苯并呋喃衍生物 (3)。(3)与水合肼、苯肼和/或盐酸羟胺的缩合得到相应的吡唑衍生物(4a、b)和异恶唑衍生物(4c)。另一方面，当化合物 3 与一些芳香醛缩合时，会产生相应的 α, β-不饱和酮衍生物（5a-e）。此外，当1进行氯磺化时，得到visnagin磺酰氯衍生物6，使用吗啉进行酰胺化，得到磺酰氯衍生物(7)。后一种化合物的碱性水解产生 7-N-吗啉代磺酰氨基苯并呋喃 (8)，其与一些芳香醛缩合产生相应的查耳酮化合物 (9a-e)。visnagin 的去甲基化提供了 norvisnagin (10)。10 与溴乙酸乙酯在无水丙酮中反应生成苯并吡喃酯衍生物 (11)，该衍生物与水合肼反应得到相应的酰肼衍生物 (12)，然后与 3,4,5-三甲氧基苯甲醛缩合得到相应的腙(13) ）。通