3-(3,4-dimethoxyphenyl)-N-(4-hydroxynaphthalen-1-yl)acrylamide | 1446203-28-6

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: 3-(3,4-dimethoxyphenyl)-N-(4-hydroxynaphthalen-1-yl)acrylamide
• CAS: 1446203-28-6
• 化学式: C₂₁H₁₉NO₄
• 分子量: 349.386
• InChiKey: CSUAPXPUECJUIQ-XYOKQWHBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.21
• 重原子数：
  26.0
• 可旋转键数：
  5.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  67.79
• 氢给体数：
  2.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  3-(3,4-dimethoxyphenyl)-N-(4-hydroxynaphthalen-1-yl)acrylamide 在 sodium periodate 、 silica gel 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以80%的产率得到(2E,NE)-3-(3,4-dimethoxyphenyl)-N-(4-oxonaphthalen-1(4H)-ylidene)acrylamide
  参考文献：
  名称：

  Synthesis and biological evaluation of N-(4-hydroxy-3-mercaptonaphthalen-1-yl)amides as inhibitors of angiogenesis and tumor growth

  摘要：

  A series of N-(4-hydroxy-3-mercaptonaphthalen-1-yl)amides were synthesized and investigated for their in vitro antiangiogenic activity. Among these compounds, 6d, which possesses an ortho-nitro group at the benzene ring, exhibited potent inhibitory effect on the proliferation of HUVECs, A549, K562, PC-3, HGT116, MDA-MB-231 and MCF-7 cells (IC50 = 5.34, 40.53, 10.81, 52.52, 10.19, 21.37 and 2.81 mu M, respectively). Meanwhile, compound 6d inhibited in vitro angiogenesis markedly in both HUVECs tube formation assay and the rat thoracic aorta rings test. Further kinase assay study showed that compound 6d had good VEGFR2, ALK, AKT1 and ABL inhibitory activities and moderate EGFR and PDGFR-beta inhibitory activities. The data supports the further investigation of this class of compounds as potential antiangiogenic and anticancer agents. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.03.043
• 作为产物：
  描述：

  4-硝基-1-萘酚 在 palladium on activated charcoal 、 氢气 、 碳酸氢钠 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， 反应 17.0h， 生成 3-(3,4-dimethoxyphenyl)-N-(4-hydroxynaphthalen-1-yl)acrylamide
  参考文献：
  名称：

  Synthesis and biological evaluation of N-(4-hydroxy-3-mercaptonaphthalen-1-yl)amides as inhibitors of angiogenesis and tumor growth

  摘要：

  A series of N-(4-hydroxy-3-mercaptonaphthalen-1-yl)amides were synthesized and investigated for their in vitro antiangiogenic activity. Among these compounds, 6d, which possesses an ortho-nitro group at the benzene ring, exhibited potent inhibitory effect on the proliferation of HUVECs, A549, K562, PC-3, HGT116, MDA-MB-231 and MCF-7 cells (IC50 = 5.34, 40.53, 10.81, 52.52, 10.19, 21.37 and 2.81 mu M, respectively). Meanwhile, compound 6d inhibited in vitro angiogenesis markedly in both HUVECs tube formation assay and the rat thoracic aorta rings test. Further kinase assay study showed that compound 6d had good VEGFR2, ALK, AKT1 and ABL inhibitory activities and moderate EGFR and PDGFR-beta inhibitory activities. The data supports the further investigation of this class of compounds as potential antiangiogenic and anticancer agents. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.03.043