(Z)-(2-naphthyl)(2,3,4-trimethoxyphenyl)methanone hydrazone | 1085752-48-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (Z)-(2-naphthyl)(2,3,4-trimethoxyphenyl)methanone hydrazone
• 英文别名: (Z)-[naphthalen-2-yl-(2,3,4-trimethoxyphenyl)methylidene]hydrazine
• CAS: 1085752-48-2
• 化学式: C₂₀H₂₀N₂O₃
• 分子量: 336.39
• InChiKey: RIIMGZMVCJPEBJ-PYCFMQQDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 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：
  66.1
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (Z)-(2-naphthyl)(2,3,4-trimethoxyphenyl)methanone hydrazone 、 乙酸酐 在 吡啶 作用下， 以80%的产率得到(Z)-(2-naphthyl)(2,3,4-trimethoxyphenyl)methanone acetylhydrazone
  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
• 作为产物：
  描述：

  (2-naphthyl)(2,3,4-trimethoxyphenyl)methanone 在 溶剂黄146 、 肼 作用下， 以 甲醇 、 水 为溶剂， 以92%的产率得到(Z)-(2-naphthyl)(2,3,4-trimethoxyphenyl)methanone hydrazone
  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

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.