(1-ethyl-1H-indol-5-yl)(3,4,5-trimethoxyphenyl)methanone O-acetyl oxime | 1043875-07-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: (1-ethyl-1H-indol-5-yl)(3,4,5-trimethoxyphenyl)methanone O-acetyl oxime
• 英文别名: [[(1-ethylindol-5-yl)-(3,4,5-trimethoxyphenyl)methylidene]amino] acetate
• CAS: 1043875-07-5
• 化学式: C₂₂H₂₄N₂O₅
• 分子量: 396.443
• InChiKey: AFFITFSHWMQATP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  29
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  71.3
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (1-ethyl-1H-indol-5-yl)(3,4,5-trimethoxyphenyl)methanone O-acetyl oxime 在 sodium hydroxide 作用下， 以 甲醇 为溶剂， 生成 (Z)-(1-ethyl-1H-indol-5-yl)(3,4,5-trimethoxyphenyl)methanone oxime 、 (NE)-N-[(1-ethylindol-5-yl)-(3,4,5-trimethoxyphenyl)methylidene]hydroxylamine
  参考文献：
  名称：

  Diarylmethyloxime and hydrazone derivatives with 5-indolyl moieties as potent inhibitors of tubulin polymerization

  摘要：

  We describe the synthesis and biological evaluation of a series of diarylmethyloxime and diarylmethylhydrazone analogues that contain an indole ring and different modi. cations on the nitrogen of the bridge. Several compounds showed potent tubulin polymerization inhibitory action as well as cytotoxic activity against cancer cell lines. The N-methyl-5-indolyl substituted analogues are more potent than ethyl substituted ones. The most potent inhibitors of tubulin polymerization are the diarylketones and the diaryloximes. The cytotoxicity against several cancer cell lines is lower for the oximes than for the ketones. Other substitutions on the imine nitrogen greatly reduce the tubulin inhibitory and/or cytotoxic potencies. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2008.04.054