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

中文名称
——
中文别名
——
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
2-(4-hydroxyphenyl)-6-methoxy-3-(3,4,5-trimethoxybenzoyl)benzo[b]furan化学式
CAS
1319803-94-5
化学式
C25H22O7
mdl
——
分子量
434.445
InChiKey
SLDDFPRQAVJYIJ-UHFFFAOYSA-N
BEILSTEIN
——
EINECS
——
  • 物化性质
  • 计算性质
  • ADMET
  • 安全信息
  • SDS
  • 制备方法与用途
  • 上下游信息
  • 反应信息
  • 文献信息
  • 表征谱图
  • 同类化合物
  • 相关功能分类
  • 相关结构分类

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
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