7-isopropoxy-2-(3-isopropoxy-4-methoxyphenyl)-6-methoxy-3-(3,4,5-trimethoxybenzoyl)benzo[b]furan | 1319803-92-3

• 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: 7-isopropoxy-2-(3-isopropoxy-4-methoxyphenyl)-6-methoxy-3-(3,4,5-trimethoxybenzoyl)benzo[b]furan
• CAS: 1319803-92-3
• 化学式: C₃₂H₃₆O₉
• 分子量: 564.632
• InChiKey: OPYHEYFFBBCNKW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.95
• 重原子数：
  41.0
• 可旋转键数：
  12.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.34
• 拓扑面积：
  94.82
• 氢给体数：
  0.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  7-isopropoxy-2-(3-isopropoxy-4-methoxyphenyl)-6-methoxy-3-(3,4,5-trimethoxybenzoyl)benzo[b]furan 在 aluminum (III) chloride 作用下， 以 二氯甲烷 为溶剂， 反应 5.33h， 以51%的产率得到7-hydroxy-2-(3-hydroxy-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
• 作为产物：
  描述：

  5-碘-1,2,3-三甲氧基苯 、 2-isopropoxy-3-methoxy-6-iodophenol 、 一氧化碳 、 3-isopropoxy-4-methoxyphenyl acetylene 在 bis-triphenylphosphine-palladium(II) chloride 、 甲基氯化镁 作用下， 以 四氢呋喃 、 二甲基亚砜 为溶剂， 以46%的产率得到7-isopropoxy-2-(3-isopropoxy-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