2-amino-4-(4-bromophenyl)-5-hydroxy-6-oxo-8-phenyl-4H-pyrano[3,2-g]chromene-3-carbonitrile

• 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-amino-4-(4-bromophenyl)-5-hydroxy-6-oxo-8-phenyl-4H-pyrano[3,2-g]chromene-3-carbonitrile
• 化学式: C₂₅H₁₅BrN₂O₄
• 分子量: 487.309
• InChiKey: RRBCOXIAGAHGNK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.15
• 重原子数：
  32.0
• 可旋转键数：
  2.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.04
• 拓扑面积：
  109.48
• 氢给体数：
  2.0
• 氢受体数：
  6.0

反应信息

• 作为产物：
  描述：

  白杨素 、 2-[((4-溴苯基)亚甲基]丙二腈 在 calcium hydroxide 作用下， 以 甲醇 为溶剂， 反应 8.0h， 以90%的产率得到2-amino-4-(4-bromophenyl)-5-hydroxy-6-oxo-8-phenyl-4H-pyrano[3,2-g]chromene-3-carbonitrile
  参考文献：
  名称：

  Regioselective synthesis and evaluation of 2-amino 3-cyano chromene-chrysin hybrids as potential anticancer agents

  摘要：

  The first example of Ca(OH)(2)-activated p-regioselective synthesis of chrysin-fused chromene was reported through a cascade Michael/cyclization of chrysin and arylidenemalononitrile. The newly synthesized structurally diverse 2-amino 3-cyano chromene-chrysin hybrids 3 were evaluated for their in vitro anticancer activity, and some of the compounds showed stronger anti-proliferative activity against K562, PC-3, A549 and NCI-H1299 than parent compound chrysin, and demonstrated equipotent potency compared with the reference drug of cisplatin. In particular, compound 3h had the highest cytotoxicity towards K562 cells (IC50 = 6.41 mu M). Furthermore, compound 3h induced apoptosis of K562 cells in a concentration-dependent manner, as well as induced the apoptosis possibly through promoting the formation of apoptotic DNA of cancer cell via the intrinsic apoptotic pathway. Thus, our results provide in vitro evidence that compound 3h may be a potential candidate for the development of new anti-tumour drugs.

  DOI：

  10.1016/j.bmcl.2020.127087

文献信息

• Regioselective synthesis and evaluation of 2-amino 3-cyano chromene-chrysin hybrids as potential anticancer agents
  作者：Hui-Juan Wang、Yan-You Zhou、Xiong-Li Liu、Wen-Hui Zhang、Shuang Chen、Xiong-Wei Liu、Ying Zhou

  DOI：10.1016/j.bmcl.2020.127087

  日期：2020.5

  The first example of Ca(OH)(2)-activated p-regioselective synthesis of chrysin-fused chromene was reported through a cascade Michael/cyclization of chrysin and arylidenemalononitrile. The newly synthesized structurally diverse 2-amino 3-cyano chromene-chrysin hybrids 3 were evaluated for their in vitro anticancer activity, and some of the compounds showed stronger anti-proliferative activity against K562, PC-3, A549 and NCI-H1299 than parent compound chrysin, and demonstrated equipotent potency compared with the reference drug of cisplatin. In particular, compound 3h had the highest cytotoxicity towards K562 cells (IC50 = 6.41 mu M). Furthermore, compound 3h induced apoptosis of K562 cells in a concentration-dependent manner, as well as induced the apoptosis possibly through promoting the formation of apoptotic DNA of cancer cell via the intrinsic apoptotic pathway. Thus, our results provide in vitro evidence that compound 3h may be a potential candidate for the development of new anti-tumour drugs.