2-(4-cyanophenyl)-8-ethoxy-3-nitro-2H-chromene | 1435972-50-1

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 黄酮类化合物
• 英文名称: 2-(4-cyanophenyl)-8-ethoxy-3-nitro-2H-chromene
• 英文别名: 4-(8-ethoxy-3-nitro-2H-chromen-2-yl)benzonitrile
• CAS: 1435972-50-1
• 化学式: C₁₈H₁₄N₂O₄
• 分子量: 322.32
• InChiKey: VLGPWPYBGFYYLW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  24
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  88.1
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  反-4-(2-硝基乙烯基)苯甲腈 、 3-乙氧基水杨醛 在 三乙胺 、 L-脯氨酸 作用下， 以 甲苯 为溶剂， 反应 24.0h， 以81%的产率得到2-(4-cyanophenyl)-8-ethoxy-3-nitro-2H-chromene
  参考文献：
  名称：

  Preparation of S14161 and its analogues and the discovery of 6-bromo-8-ethoxy-3-nitro-2H-chromene as a more potent antitumor agent in vitro

  摘要：

  The small chemical compound 8-ethoxy-2-(4-fluorophenyl)-3-nitro-2H-chromene (S14161) was recently identified as an inhibitor of the phosphoinositide 3-kinase (PI3K). In the present study, we designed a novel synthesis of S14161 and prepared a series of its analogues via the oxa-Michael-Henry reaction in the presence of catalytic amounts of L-proline and triethylamine. Further structural simplification led to the identification of 6-bromo-8-ethoxy-3-nitro-2H-chromene (BENC-511) that exhibited potent antiproliferative activities against a panel of 12 tumor cell lines. Compared with S14161, BENC-511 was more potent in blocking the AKT phosphorylation and inducing cancer cell apoptosis. BENC-511 also displayed more potent effects on human umbilical vein epithelial cells (HUVEC) migration, suggesting its anti-angiogenesis activity. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.03.097

文献信息

• Preparation of S14161 and its analogues and the discovery of 6-bromo-8-ethoxy-3-nitro-2H-chromene as a more potent antitumor agent in vitro
  作者：Shu-Qiang Yin、Min Shi、Ting-Ting Kong、Cheng-Mei Zhang、Kunkun Han、Biyin Cao、Zubin Zhang、Xiaolin Du、Long-Qian Tang、Xinliang Mao、Zhao-Peng Liu

  DOI：10.1016/j.bmcl.2013.03.097

  日期：2013.6

  The small chemical compound 8-ethoxy-2-(4-fluorophenyl)-3-nitro-2H-chromene (S14161) was recently identified as an inhibitor of the phosphoinositide 3-kinase (PI3K). In the present study, we designed a novel synthesis of S14161 and prepared a series of its analogues via the oxa-Michael-Henry reaction in the presence of catalytic amounts of L-proline and triethylamine. Further structural simplification led to the identification of 6-bromo-8-ethoxy-3-nitro-2H-chromene (BENC-511) that exhibited potent antiproliferative activities against a panel of 12 tumor cell lines. Compared with S14161, BENC-511 was more potent in blocking the AKT phosphorylation and inducing cancer cell apoptosis. BENC-511 also displayed more potent effects on human umbilical vein epithelial cells (HUVEC) migration, suggesting its anti-angiogenesis activity. (C) 2013 Elsevier Ltd. All rights reserved.