7-(3,4-dihydro-8-isopentyl-2-oxo-2H-chromen-7-yloxy)heptanoic acid | 1335107-56-6

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 3,4-二氢香豆素
• 英文名称: 7-(3,4-dihydro-8-isopentyl-2-oxo-2H-chromen-7-yloxy)heptanoic acid
• 英文别名: 7-[[8-(3-Methylbutyl)-2-oxo-3,4-dihydrochromen-7-yl]oxy]heptanoic acid
• CAS: 1335107-56-6
• 化学式: C₂₁H₃₀O₅
• 分子量: 362.466
• InChiKey: DAEJETOGQCARHQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  26
• 可旋转键数：
  11
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  72.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  7-(3,4-dihydro-8-isopentyl-2-oxo-2H-chromen-7-yloxy)heptanoic acid 在 氯甲酸乙酯 、 三乙胺 、 盐酸羟胺 、 potassium hydroxide 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 4.0h， 以63%的产率得到N-hydroxy-7-(3-hydroxy-4-(2-hydroxycarbamoylethyl)-2-isopentyl-phenoxy)heptanamide
  参考文献：
  名称：

  Synthesis and evaluation of aliphatic-chain hydroxamates capped with osthole derivatives as histone deacetylase inhibitors

  摘要：

  Our previous studies have demonstrated that osthole, a Chinese herbal compound, could be incorporated into the hydroxycinnamide scaffold of LBH-589, a potent HDAC inhibitor, as an effective hydrophobic cap; the resulting compounds showed significant potency against several HDAC isoforms. Here, we presented a series of osthole derivatives fused with the aliphatic-hydroxamate core of suberoylanilide hydroxamic acid (SAHA), a clinically-approved HDAC inhibitor. Several compounds showed potent activity against nuclear HDACs. Further assays against individual HDAC isoforms revealed that some compounds showed not only SAHA-like activity towards HDAC1, -4 and -6, they inhibited HDAC8 by log difference than SAHA and thus exhibited a broader HDAC inhibition spectrum. Among them, compound 6g showed potent antiproliferative effect on several human cancer cell lines. (C) 2011 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2011.06.002
• 作为产物：
  描述：

  蛇床子提取物 在 甲醇 、 18-冠醚-6 、 palladium 10% on activated carbon 、 氢气 、 三溴化硼 、 四丁基碘化铵 、 potassium carbonate 、 lithium hydroxide 作用下， 以 二氯甲烷 、 乙酸乙酯 、 丙酮 为溶剂， 63.0 ℃ 、101.33 kPa 条件下， 反应 23.0h， 生成 7-(3,4-dihydro-8-isopentyl-2-oxo-2H-chromen-7-yloxy)heptanoic acid
  参考文献：
  名称：

  Synthesis and evaluation of aliphatic-chain hydroxamates capped with osthole derivatives as histone deacetylase inhibitors

  摘要：

  Our previous studies have demonstrated that osthole, a Chinese herbal compound, could be incorporated into the hydroxycinnamide scaffold of LBH-589, a potent HDAC inhibitor, as an effective hydrophobic cap; the resulting compounds showed significant potency against several HDAC isoforms. Here, we presented a series of osthole derivatives fused with the aliphatic-hydroxamate core of suberoylanilide hydroxamic acid (SAHA), a clinically-approved HDAC inhibitor. Several compounds showed potent activity against nuclear HDACs. Further assays against individual HDAC isoforms revealed that some compounds showed not only SAHA-like activity towards HDAC1, -4 and -6, they inhibited HDAC8 by log difference than SAHA and thus exhibited a broader HDAC inhibition spectrum. Among them, compound 6g showed potent antiproliferative effect on several human cancer cell lines. (C) 2011 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2011.06.002