(2-naphthyl)(2,3,4-trimethoxyphenyl)methyl acetate

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (2-naphthyl)(2,3,4-trimethoxyphenyl)methyl acetate
• 英文别名: [Naphthalen-2-yl-(2,3,4-trimethoxyphenyl)methyl] acetate
• 化学式: C₂₂H₂₂O₅
• 分子量: 366.414
• InChiKey: WBXRDCCQRXCZNY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  27
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  54
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  1,2,3-三甲氧基苯 在 吡啶 、 N-溴代丁二酰亚胺(NBS) 、 正丁基锂 作用下， 以 四氢呋喃 、 四氯化碳 为溶剂， 生成 (2-naphthyl)(2,3,4-trimethoxyphenyl)methyl acetate
  参考文献：
  名称：

  Synthesis and biological activity of naphthalene analogues of phenstatins: Naphthylphenstatins

  摘要：

  Novel phenstatin analogues with a 2-naphthyl moiety combined with either a 2,3,4- or a 3,4,5-trimethoxyphenyl ring have been synthesized, and their tubulin polymerization inhibiting and cytotoxic activities have been evaluated. The 2-naphthyl ring is a better replacement for the 3-hydroxy-4-methoxyphenyl ring in the phenstatin series than in the combretastatin series. For the naphthylphenstatins, the carbonyl is required, and the preferred orientation of the trimethoxyphenyl ring is the one found in combretastatins. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.03.082

文献信息

• Naphthylphenstatins as tubulin ligands: Synthesis and biological evaluation
  作者：Concepción Álvarez、Raquel Álvarez、Purificación Corchete、Concepción Pérez-Melero、Rafael Peláez、Manuel Medarde

  DOI：10.1016/j.bmc.2008.08.040

  日期：2008.10

  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.
• Synthesis and biological activity of naphthalene analogues of phenstatins: Naphthylphenstatins
  作者：Concepción Álvarez、Raquel Álvarez、Purificación Corchete、Concepción Pérez-Melero、Rafael Peláez、Manuel Medarde

  DOI：10.1016/j.bmcl.2007.03.082

  日期：2007.6

  Novel phenstatin analogues with a 2-naphthyl moiety combined with either a 2,3,4- or a 3,4,5-trimethoxyphenyl ring have been synthesized, and their tubulin polymerization inhibiting and cytotoxic activities have been evaluated. The 2-naphthyl ring is a better replacement for the 3-hydroxy-4-methoxyphenyl ring in the phenstatin series than in the combretastatin series. For the naphthylphenstatins, the carbonyl is required, and the preferred orientation of the trimethoxyphenyl ring is the one found in combretastatins. (c) 2007 Elsevier Ltd. All rights reserved.