(2-naphthyl)(3,4,5-trimethoxyphenyl)methanone oxime | 1085752-14-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (2-naphthyl)(3,4,5-trimethoxyphenyl)methanone oxime
• 英文别名: N-[naphthalen-2-yl-(3,4,5-trimethoxyphenyl)methylidene]hydroxylamine
• CAS: 1085752-14-2
• 化学式: C₂₀H₁₉NO₄
• 分子量: 337.375
• InChiKey: KILOMLZASNVJLX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  25
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  60.3
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (2-naphthyl)(3,4,5-trimethoxyphenyl)methanone oxime 、 二碳酸二叔丁酯 在 sodium carbonate 作用下， 以 1,4-二氧六环 、 水 为溶剂， 反应 48.0h， 生成 (Z)-(2-naphthyl)(3,4,5-trimethoxyphenyl)methanone tert-butoxycarbonyloxime 、 (E)-(2-naphthyl)(3,4,5-trimethoxyphenyl)methanone tert-butoxycarbonyloxime
  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