5-methoxy-1-(4-methoxybenzyl)-1,3-dihydroindol-2-one | 1359986-89-2

• 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: 5-methoxy-1-(4-methoxybenzyl)-1,3-dihydroindol-2-one
• 英文别名: 5-methoxy-1-(4-methoxybenzyl)-2-indolinone
• CAS: 1359986-89-2
• 化学式: C₁₇H₁₇NO₃
• 分子量: 283.327
• InChiKey: BPKXZNMCCCJENA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.79
• 重原子数：
  21.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  38.77
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  5-methoxy-1-(4-methoxybenzyl)-1,3-dihydroindol-2-one 、 3,4,5-三甲氧基苯甲醛 在 sodium acetate 作用下， 以 溶剂黄146 为溶剂， 反应 168.0h， 以30%的产率得到(3E)-5-methoxy-1-[(4-methoxyphenyl)methyl]-3-[(3,4,5-trimethoxyphenyl)methylidene]indol-2-one
  参考文献：
  名称：

  Cytotoxic activities of substituted 3-(3,4,5-trimethoxybenzylidene)-1,3-dihydroindol-2-ones and studies on their mechanisms of action

  摘要：

  The synthesis of new trimethoxybenzylidene-indolinones is reported. Their cytotoxic activity was evaluated according to Developmental Therapeutics Program, National Cancer Institute, Bethesda, MD, drug screen protocols. The study of the mechanism of action suggests that inhibition of Nox4 in B1647 cells (acute myeloid leukemia) could contribute to the antiproliferative effect of some compounds. Moreover, inhibition of tubulin assembly was observed for the most cytotoxic compound, and the structural basis for this activity was delineated by binding models. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.03.033
• 作为产物：
  描述：

  1-(p-methoxybenzyl)-5-methoxyisatin 在 一水合肼 作用下， 反应 5.0h， 以63%的产率得到5-methoxy-1-(4-methoxybenzyl)-1,3-dihydroindol-2-one
  参考文献：
  名称：

  Substituted 3-(5-Imidazo[2,1-b]thiazolylmethylene)-2-indolinones and Analogues: Synthesis, Cytotoxic Activity, and Study of the Mechanism of Action

  摘要：

  The synthesis of substituted 3-(5-imidazo[2,1-b]thiazolylmethylene)-2-indolinones and analogues is reported. Their cytotoxic activity was evaluated according to protocols available at the National Cancer Institute (NCI), Bethesda, MD. The action of selected compounds was examined for potential inhibition of tubulin assembly in comparison with the potent colchicine site agent combretastatin A-4. The most potent compounds also strongly and selectively inhibited the phosphorylation of the oncoprotein kinase Akt in cancer cells. The effect of the most interesting compounds was examined on the growth of HT-29 colon cancer cells. These compounds caused the cells to arrest in the G2/M phase of the cell cycle, as would be expected for inhibitors of tubulin assembly.

  DOI：

  10.1021/jm2012694