(2E)-1-(1,3-benzodioxol-5-yl)-3-(quinoxalin-6-yl)prop-2-en-1-one | 1357063-33-2

• 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: (2E)-1-(1,3-benzodioxol-5-yl)-3-(quinoxalin-6-yl)prop-2-en-1-one
• 英文别名: (E)-1-(benzo[d][1,3]dioxol-5-yl)-3-(quinoxalin-6-yl)prop-2-en-1-one；(E)-1-(1,3-benzodioxol-5-yl)-3-quinoxalin-6-ylprop-2-en-1-one
• CAS: 1357063-33-2
• 化学式: C₁₈H₁₂N₂O₃
• 分子量: 304.305
• InChiKey: DLTKYVRDIHVYMD-GORDUTHDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  61.3
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  (喹噁啉-6-基)甲醇 在 pyridinium chlorochromate 、 potassium hydroxide 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 24.0h， 生成 (2E)-1-(1,3-benzodioxol-5-yl)-3-(quinoxalin-6-yl)prop-2-en-1-one
  参考文献：
  名称：

  Activity of novel quinoxaline-derived chalcones on in vitro glioma cell proliferation

  摘要：

  Gliomas are the most common and devastating tumors of the central nervous system (CNS). Many pieces of evidence point out the relevance of natural compounds for cancer therapy and prevention, including chalcones. In the present study, eight synthetic quinoxaline-derived chalcones, structurally based on the selective PI3K gamma inhibitor AS605240, were evaluated for anti-proliferative activity and viability inhibition using glioma cell lines from human and rat origin (U-138 MG and C6, respectively), at different time-periods of incubation and concentrations. The results revealed that four chalcones (compounds 1, 6, 7 and 8), which present methoxy groups at A-ring, displayed higher efficacies and potencies, being able to inhibit either cell proliferation or viability, in a time- and concentration-dependent manner, with an efficacy that was greater than that seen for the positive control compound AS605240. Flow cytometry analysis demonstrated that incubation of C6 cells with compound 6 led to Cl phase arrest, likely indicating an interference with apoptosis. Furthermore, compound 6 was able to visibly inhibit ART activation, allied to the stimulation of ERR MAP-kinase. The chalcones tested herein, especially those displaying a methoxy substituent, might well represent promising molecules for the adjuvant treatment of glioma progression. (C) 2011 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2011.12.023

文献信息

• Activity of novel quinoxaline-derived chalcones on in vitro glioma cell proliferation
  作者：Tânia R. Mielcke、Alessandra Mascarello、Eduardo Filippi-Chiela、Rafael F. Zanin、Guido Lenz、Paulo César Leal、Louise D. Chirardia、Rosendo A. Yunes、Ricardo J. Nunes、Ana M.O. Battastini、Fernanda B. Morrone、Maria M. Campos

  DOI：10.1016/j.ejmech.2011.12.023

  日期：2012.2

  Gliomas are the most common and devastating tumors of the central nervous system (CNS). Many pieces of evidence point out the relevance of natural compounds for cancer therapy and prevention, including chalcones. In the present study, eight synthetic quinoxaline-derived chalcones, structurally based on the selective PI3K gamma inhibitor AS605240, were evaluated for anti-proliferative activity and viability inhibition using glioma cell lines from human and rat origin (U-138 MG and C6, respectively), at different time-periods of incubation and concentrations. The results revealed that four chalcones (compounds 1, 6, 7 and 8), which present methoxy groups at A-ring, displayed higher efficacies and potencies, being able to inhibit either cell proliferation or viability, in a time- and concentration-dependent manner, with an efficacy that was greater than that seen for the positive control compound AS605240. Flow cytometry analysis demonstrated that incubation of C6 cells with compound 6 led to Cl phase arrest, likely indicating an interference with apoptosis. Furthermore, compound 6 was able to visibly inhibit ART activation, allied to the stimulation of ERR MAP-kinase. The chalcones tested herein, especially those displaying a methoxy substituent, might well represent promising molecules for the adjuvant treatment of glioma progression. (C) 2011 Elsevier Masson SAS. All rights reserved.