3-(4-Chlorophenyl)-1-(6-hydroxy-4-methoxy-1-benzofuran-5-yl)prop-2-en-1-one | 444107-39-5

• 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: 3-(4-Chlorophenyl)-1-(6-hydroxy-4-methoxy-1-benzofuran-5-yl)prop-2-en-1-one
• CAS: 444107-39-5
• 化学式: C₁₈H₁₃ClO₄
• 分子量: 328.752
• InChiKey: KVPPJWSRECHASD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 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：

  3-(4-Chlorophenyl)-1-(6-hydroxy-4-methoxy-1-benzofuran-5-yl)prop-2-en-1-one 在 potassium dichromate 、 selenium(IV) oxide 、 硫酸 、 potassium carbonate 、 溶剂黄146 、 N,N-二乙基苯胺 作用下， 以 丙酮 、 正丁醇 为溶剂， 反应 42.0h， 生成 8-allyl-2-(4-chlorophenyl)-7-hydroxy-5-methoxy-4-oxo-4H-chromene-6-carbaldehyde
  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 hydroxide 、 sodium hydroxide 作用下， 以 乙醇 为溶剂， 反应 25.0h， 生成 3-(4-Chlorophenyl)-1-(6-hydroxy-4-methoxy-1-benzofuran-5-yl)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

• Celecoxib analogs bearing benzofuran moiety as cyclooxygenase-2 inhibitors: Design, synthesis and evaluation as potential anti-inflammatory agents
  作者：Ghaneya Sayed Hassan、Sahar Mahmoud Abou-Seri、Gehan Kamel、Mamdouh Moawad Ali

  DOI：10.1016/j.ejmech.2014.02.033

  日期：2014.4

  The most potent and selective COX-2 inhibitors – compounds 3c, 3d, 3e, 9c and 9d – were assessed for their anti-inflammatory activity and ulcerogenic liability in vivo. The 3-(pyridin-3-yl)pyrazole derivatives 3c and 3e exhibited the highest anti-inflammatory activity, that is equipotent to celecoxib. Furthermore, the tested compounds proved to have better gastric safety profile compared to celecoxib

  合成了具有苯并呋喃部分3a - e和9a - d的新系列塞来昔布类似物，并对其体外COX-1 / COX-2抑制活性进行了评估。评估了最有效和选择性最强的COX-2抑制剂-化合物3c，3d，3e，9c和9d的体内抗炎活性和致溃疡作用。3-（吡啶-3-基）吡唑衍生物3c和3e具有最高的抗炎活性，相当于塞来昔布。此外，与塞来昔布相比，被测化合物具有更好的胃安全性。特别地，相对于参考药物，化合物3e显示出致溃疡的可能性降低了约40％。最后，在COX-2活性位点和药物相似性研究中对新化合物进行了分子对接模拟，结果与所获得的药理生物学结果吻合良好。
• 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.