2-(3-amino-4-methoxyphenyl)-6-methoxy-3-(3,4,5-trimethoxybenzoyl)benzo[b]furan | 1319803-93-4

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 2-芳基苯并呋喃类黄酮
• 英文名称: 2-(3-amino-4-methoxyphenyl)-6-methoxy-3-(3,4,5-trimethoxybenzoyl)benzo[b]furan
• 英文别名: [2-(3-Amino-4-methoxyphenyl)-6-methoxy-1-benzofuran-3-yl]-(3,4,5-trimethoxyphenyl)methanone
• CAS: 1319803-93-4
• 化学式: C₂₆H₂₅NO₇
• 分子量: 463.487
• InChiKey: CMEFMOKLOSBTSU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  34
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  102
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  4-碘-2-甲氧基苯胺 在 盐酸 、 bis-triphenylphosphine-palladium(II) chloride 、 potassium fluoride 、 copper(l) iodide 、 palladium 10% on activated carbon 、 氢气 、 甲基氯化镁 、 potassium carbonate 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 、 乙酸乙酯 、 N,N-二甲基甲酰胺 为溶剂， 反应 10.0h， 生成 2-(3-amino-4-methoxyphenyl)-6-methoxy-3-(3,4,5-trimethoxybenzoyl)benzo[b]furan
  参考文献：
  名称：

  Discovery of 7-Hydroxy-6-methoxy-2-methyl-3-(3,4,5-trimethoxybenzoyl)benzo[b]furan (BNC105), a Tubulin Polymerization Inhibitor with Potent Antiproliferative and Tumor Vascular Disrupting Properties

  摘要：

  A structure activity relationship (SAR) guided design of novel tubulin polymerization inhibitors has resulted in a series of benzo[b]furans with exceptional potency toward cancer cells and activated endothelial cells. The potency of early lead compounds has been substantially improved through the synergistic effect of introducing a conformational bias and additional hydrogen bond donor to the pharmacophore. Screening of a focused library of potent tubulin polymerization inhibitors for selectivity against cancer cells and activated endothelial cells over quiescent endothelial cells has afforded 7-hydroxy-6-methoxy-2-methyl-3-(3,4,5-trimethoxybenzoyl)benzo-[b]furan (BNC105, 8) as a potent and selective antiproliferative. Because of poor solubility, 8 is administered as its disodium phosphate ester prodrug 9 (BNC105P), which is rapidly cleaved in vivo to return the active 8. 9 exhibits both superior vascular disrupting and tumor growth inhibitory properties compared with the benchmark agent combretastatin A-4 disodium phosphate 5 (CA4P).

  DOI：

  10.1021/jm200454y