N-(2-naphthyl)-N-(3,4,5-trimethoxybenzyl)acetamide | 1085752-40-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: N-(2-naphthyl)-N-(3,4,5-trimethoxybenzyl)acetamide
• CAS: 1085752-40-4
• 化学式: C₂₂H₂₃NO₄
• 分子量: 365.429
• InChiKey: UUWAMBCXDIWIGD-UHFFFAOYSA-N

反应信息

• 作为产物：
  描述：

  (2-naphthyl)(3,4,5-trimethoxyphenyl)methanone oxime 、 乙酸酐 在 lithium aluminium tetrahydride 、 吡啶 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以28%的产率得到N-(2-naphthyl)-N-(3,4,5-trimethoxybenzyl)acetamide
  参考文献：
  名称：

  Naphthylphenstatins as tubulin ligands: Synthesis and biological evaluation

  摘要：

  A new family of naphthalenic analogues of phenstatins with modi. cations on the ketone-bridge has been synthesised. The synthesised compounds have been assayed for tubulin polymerisation inhibitory activity as well as for cytotoxic activity against cancer cell lines. The naphthalene has been confirmed as a good surrogate for the isovanillin moiety (3-hydroxy-4-methoxyphenyl) of phenstatin, when combined with the 3,4,5-trimethoxyphenyl ring, but not when combines with the 2,3,4-trimethoxyphenyl ring. Binding models for the synthesised compounds have been generated and analysed in terms of a pharmacophore proposed for colchicine site ligands. The ketone is the optimal bridge substitution but E-acetyloximes or acetylhydrazones are also tolerated. Significant differences with indole substituted phenstatins are observed and discussed. (C) 2008 Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmc.2008.08.040