N-(3-((1H-1,2,4-triazol-5-yl)thio)-4-hydroxynaphthalen-1-yl)-3-methylbenzamide

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: N-(3-((1H-1,2,4-triazol-5-yl)thio)-4-hydroxynaphthalen-1-yl)-3-methylbenzamide
• 化学式: C₂₀H₁₆N₄O₂S
• 分子量: 376.439
• InChiKey: PCRYJPDCPDBGQL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.38
• 重原子数：
  27.0
• 可旋转键数：
  4.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  90.9
• 氢给体数：
  3.0
• 氢受体数：
  5.0

反应信息

• 作为产物：
  描述：

  硝基萘 在 sodium periodate 、 palladium on activated charcoal 、 氢气 、 silica gel 、 碳酸氢钠 、 potassium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 、 二甲基亚砜 、 N,N-二甲基甲酰胺 为溶剂， 反应 25.08h， 生成 N-(3-((1H-1,2,4-triazol-5-yl)thio)-4-hydroxynaphthalen-1-yl)-3-methylbenzamide
  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

文献信息

• Synthesis and biological evaluation of N-(4-hydroxy-3-mercaptonaphthalen-1-yl)amides as inhibitors of angiogenesis and tumor growth
  作者：Fuming Xu、Yuping Jia、Qingli Wen、Xuejian Wang、Lei Zhang、Yingjie Zhang、Kanghui Yang、Wenfang Xu

  DOI：10.1016/j.ejmech.2013.03.043

  日期：2013.6

  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.