2-(4-hydroxyphenyl)-6-methoxy-3-(3,4,5-trimethoxybenzoyl)benzo[b]furan | 1319803-94-5

• 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-(4-hydroxyphenyl)-6-methoxy-3-(3,4,5-trimethoxybenzoyl)benzo[b]furan
• 英文别名: [2-(4-Hydroxyphenyl)-6-methoxy-1-benzofuran-3-yl]-(3,4,5-trimethoxyphenyl)methanone
• CAS: 1319803-94-5
• 化学式: C₂₅H₂₂O₇
• 分子量: 434.445
• InChiKey: SLDDFPRQAVJYIJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  32
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  87.4
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  2-(4-benzyloxyphenyl)-6-methoxy-3-(3,4,5-trimethoxybenzoyl)benzo[b]furan 在 palladium 10% on activated carbon 、 氢气 作用下， 以 乙酸乙酯 为溶剂， 反应 1.0h， 以63%的产率得到2-(4-hydroxyphenyl)-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