7-hydroxy-3-(3-hydroxy-2,4-dimethoxyphenyl)chromen-4-one

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 异黄酮类化合物
• 英文名称: 7-hydroxy-3-(3-hydroxy-2,4-dimethoxyphenyl)chromen-4-one
• 英文别名: 4',7-dihydroxy-3',5'-dimethoxyisoflavone；7,4′‐dihydroxy‐3′,5′‐dimethoxyisoflavone；7-hydroxy-3-(4-hydroxy-3,5-dimethoxyphenyl)chromen-4-one
• 化学式: C₁₇H₁₄O₆
• 分子量: 314.295
• InChiKey: KAAIDCFNSXASKK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  85.2
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  7-benzyloxy-3-(3-benzyloxy-2,4-dimethoxyphenyl)chromen-4-one 在 氢溴酸 作用下， 以 水 为溶剂， 以95%的产率得到7-hydroxy-3-(3-hydroxy-2,4-dimethoxyphenyl)chromen-4-one
  参考文献：
  名称：

  橄榄黄异黄酮类似物的合成及生物学评价

  摘要：

  通过涉及有机铅试剂的配体偶联反应，制备了从Dalbergia oliveri Gamble分离出的Mucronulatol 1和violanone 2，以及相应的异黄酮3。生物学研究表明，仅对于异黄烷1，其对HBL100白血病细胞系具有明显的细胞毒性作用，IC 50值为5.7μM 。所有药物均会适度地抑制体外微管的组装，而与细胞毒性能力无关。天然化合物1和2没有抗菌活性，但是是尖孢镰刀菌植物致病性真菌生长的有效抑制剂。

  DOI：

  10.1016/j.tet.2007.10.030

文献信息

• A Versatile Microbial System for Biosynthesis of Novel Polyphenols with Altered Estrogen Receptor Binding Activity
  作者：Joseph A. Chemler、Chin Giaw Lim、John L. Daiss、Mattheos A.G. Koffas

  DOI：10.1016/j.chembiol.2010.03.010

  日期：2010.4

  Isoflavonoids possess enormous potential for human health with potential impact on heart disease and cancer, and some display striking affinities for steroid receptors. Synthesized primarily by legumes, isoflavonoids are present in low and variable abundance within complex mixtures, complicating efforts to assess their clinical potential. To satisfy the need for controlled, efficient, and flexible biosynthesis of isoflavonoids, a three-enzyme system has been constructed in yeast that can convert natural and synthetic flavanones into their corresponding isoflavones in practical quantities. Based on the determination of the substrate requirements of isoflavone synthase, a series of natural and nonnatural isoflavones were prepared and their binding affinities for the human estrogen receptors (ER alpha and ER beta) were determined. Structure activity relationships are suggested based on changes to binding affinities related to small variations on the isoflavone structure.
• Synthesis and biological evaluation of isoflavone analogues from Dalbergia oliveri
  作者：Sujittra Deesamer、Udom Kokpol、Warinthorn Chavasiri、Soazig Douillard、Vincent Peyrot、Nicolas Vidal、Sebastien Combes、Jean-Pierre Finet

  DOI：10.1016/j.tet.2007.10.030

  日期：2007.12

  Mucronulatol 1 and violanone 2 isolated from Dalbergia oliveri Gamble, and the corresponding isoflavone 3 were prepared by ligand coupling reactions involving organolead reagent. Biological studies have shown a significant cytotoxic effect against an HBL100 leukemia cell line only for isoflavan 1 with an IC50 value amounting to 5.7 μM. All the drugs modestly inhibit the in vitro microtubule assembly

  通过涉及有机铅试剂的配体偶联反应，制备了从Dalbergia oliveri Gamble分离出的Mucronulatol 1和violanone 2，以及相应的异黄酮3。生物学研究表明，仅对于异黄烷1，其对HBL100白血病细胞系具有明显的细胞毒性作用，IC 50值为5.7μM 。所有药物均会适度地抑制体外微管的组装，而与细胞毒性能力无关。天然化合物1和2没有抗菌活性，但是是尖孢镰刀菌植物致病性真菌生长的有效抑制剂。

表征谱图