(E)-3-phenyl-2-(2-styrylphenyl)quinazolin-4(3H)-one

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: (E)-3-phenyl-2-(2-styrylphenyl)quinazolin-4(3H)-one
• 英文别名: 3-phenyl-2-[2-[(E)-2-phenylethenyl]phenyl]quinazolin-4-one
• 化学式: C₂₈H₂₀N₂O
• 分子量: 400.48
• InChiKey: FWHVPNDOMQBZIR-FMQUCBEESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.1
• 重原子数：
  31
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  32.7
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  在 potassium tert-butylate 、 四丁基溴化铵 作用下， 以 四氢呋喃 为溶剂， 以80%的产率得到(E)-3-phenyl-2-(2-styrylphenyl)quinazolin-4(3H)-one
  参考文献：
  名称：

  Synthesis and anticancer activity of N-substituted 2-arylquinazolinones bearing trans-stilbene scaffold

  摘要：

  A novel series of 2-arylquinazolinones 7a-o bearing trans-stilbene moiety were designed, synthesized, and evaluated against human breast cancer cell lines including human breast adenocarcinoma (MCF-7 and MDA-MB-231) and human ductal breast epithelial tumor (T-47D). Among the tested compounds, the sec-butyl derivative 7h showed the best profile of activity (IC50 < 5 mu M) against all cell lines, being 2-fold more potent than standard drug, etoposide. Our investigation revealed that the cytotoxic activity was significantly affected by N3-alkyl substituents. Furthermore, the morphological analysis by acridine orange/ethidium bromide double staining test and flow cytometry analysis indicated that the prototype compound 7h can induce apoptosis in MCF-7 and MDA-MB-231 cells. (C) 2015 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2015.03.057

文献信息

• Synthesis and anticancer activity of N-substituted 2-arylquinazolinones bearing trans-stilbene scaffold
  作者：Mohammad Mahdavi、Keyvan Pedrood、Maliheh Safavi、Mina Saeedi、Mahboobeh Pordeli、Sussan Kabudanian Ardestani、Saeed Emami、Mehdi Adib、Alireza Foroumadi、Abbas Shafiee

  DOI：10.1016/j.ejmech.2015.03.057

  日期：2015.5

  A novel series of 2-arylquinazolinones 7a-o bearing trans-stilbene moiety were designed, synthesized, and evaluated against human breast cancer cell lines including human breast adenocarcinoma (MCF-7 and MDA-MB-231) and human ductal breast epithelial tumor (T-47D). Among the tested compounds, the sec-butyl derivative 7h showed the best profile of activity (IC50 < 5 mu M) against all cell lines, being 2-fold more potent than standard drug, etoposide. Our investigation revealed that the cytotoxic activity was significantly affected by N3-alkyl substituents. Furthermore, the morphological analysis by acridine orange/ethidium bromide double staining test and flow cytometry analysis indicated that the prototype compound 7h can induce apoptosis in MCF-7 and MDA-MB-231 cells. (C) 2015 Elsevier Masson SAS. All rights reserved.