N-(4-hydroxynaphthalen-1-yl)-4-methoxybenzamide

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: N-(4-hydroxynaphthalen-1-yl)-4-methoxybenzamide
• 英文别名: Pcmd-CC-jbs-224
• 化学式: C₁₈H₁₅NO₃
• 分子量: 293.322
• InChiKey: QNGPKBTZYMVTCH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  58.6
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-(4-hydroxynaphthalen-1-yl)-4-methoxybenzamide 在 sodium periodate 、 silica gel 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以85%的产率得到(E)-4-methoxy-N-(4-oxonaphthalen-1(4H)-ylidene)benzamide
  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：

  硝基萘 在 palladium on activated charcoal 、 氢气 、 碳酸氢钠 、 potassium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 水 、 二甲基亚砜 为溶剂， 反应 19.08h， 生成 N-(4-hydroxynaphthalen-1-yl)-4-methoxybenzamide
  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

• Introduction of a Hydroxy Group at the Para Position and <i>N</i>-Iodophenylation of <i>N</i>-Arylamides Using Phenyliodine(III) Bis(Trifluoroacetate)
  作者：Naoki Itoh、Takeshi Sakamoto、Etsuko Miyazawa、Yasuo Kikugawa

  DOI：10.1021/jo0260847

  日期：2002.10.1

  The reaction of anilides with phenyliodine(III) bis(trifluoroacetate) (PIFA) in trifluoroacetic acid (TFA), TFA-CHCl3, or hexafluoroisopropyl alcohol (HFIP) is described. When the acyl group of the anilide is highly electronegative, such as trifluoroacetyl, or the phenyl group is substituted with an electron-withdrawing group, the 4-iodophenyl group is transferred from PIFA to the amide nitrogen to

  描述了在三氟乙酸（TFA），TFA-CHCl3或六氟异丙醇（HFIP）中，苯甲酸酯与苯基碘（III）双（三氟乙酸酯）（PIFA）的反应。当苯胺的酰基具有高负电性时，例如三氟乙酰基，或者苯基被吸电子基团取代，则4-碘苯基从PIFA转移到酰胺氮上，得到乙酰基二芳基胺。另一方面，当酰基具有诸如4-甲氧基苯基之类的供电子功能时，或者苯基被供电子性基团取代时，三氟乙酰氧基被转移至苯胺芳环的对位。该组在后处理过程中水解产生相应的苯酚。
• 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.