7,8-dihydroxy-3',4'-dimethoxyisoflavone | 97770-37-1

• 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: 7,8-dihydroxy-3',4'-dimethoxyisoflavone
• 英文别名: 7,8-dihydroxy-3′,4′-dimethoxyisoflavone；3-(3,4-Dimethoxyphenyl)-7,8-dihydroxy-4H-1-benzopyran-4-one；3-(3,4-dimethoxyphenyl)-7,8-dihydroxychromen-4-one
• CAS: 97770-37-1
• 化学式: C₁₇H₁₄O₆
• 分子量: 314.295
• InChiKey: KILWWFPDYZRTJI-UHFFFAOYSA-N

物化性质

• 熔点：
  209-211 °C
• 沸点：
  540.4±50.0 °C(Predicted)
• 密度：
  1.402±0.06 g/cm3(Predicted)

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

• 作为反应物：
  描述：

  7,8-dihydroxy-3',4'-dimethoxyisoflavone 在 silver(l) oxide 作用下， 以 吡啶 、 甲醇 、 苯 为溶剂， 反应 20.0h， 生成 di-O-acetyl-3'-O-methylxanthocercin B
  参考文献：
  名称：

  Bezuidenhout, S. Catherine; Bezuidenhout, Barend C. B.; Brandt, E. Vincent, Journal of the Chemical Society. Perkin transactions I, 1988, p. 1237 - 1242

  摘要：

  DOI：
• 作为产物：
  描述：

  邻苯三酚 在 三氟化硼乙醚 、 甲基磺酰氯 作用下， 生成 7,8-dihydroxy-3',4'-dimethoxyisoflavone
  参考文献：
  名称：

  异黄酮的氧化二聚：葛根黄酮A及其相关化合物的合成*

  摘要：

  Kudzuisoflavone-A是在氯化亚铜存在下通过大豆苷元的氧化二聚作用成功合成的。当用三氟乙酸th处理时，适当取代的异黄酮也进行区域选择性氧化二聚，从而以高收率得到新的6'，6'''-二异黄酮。提出了区域选择性的基本原理。

  DOI：

  10.1071/ch12108

文献信息

• Synthesis of Various Kinds of Isoflavones, Isoflavanes, and Biphenyl-Ketones and Their 1,1-Diphenyl-2-picrylhydrazyl Radical-Scavenging Activities
  作者：Hideyuki Goto、Yoshiyasu Terao、Shuji Akai

  DOI：10.1248/cpb.57.346

  日期：——

  Forty-eight kinds of isoflavones (8), thirty-one isoflavanes (9), and forty-seven biphenyl-ketones (10, 10′) were synthesized from eleven kinds of substituted phenols (11) and six phenylacetic acids (12). Among them, seventy-five compounds are new. The radical scavenging activities of these compounds were evaluated using 1,1-diphenyl-2-picrylhydrazyl (DPPH) at pH 6.0. We found that thirty-nine out of forty-three compounds having a catechol moiety on either the A- or the B-ring exhibited a high activity (ED50=12—54 μM) similar to that of catechin. In these cases, the remaining part of their structure seemed to have little effect on their activity. Many 6- or 8-hydroxyisoflavanes (9E—I) and their biphenyl-ketone derivatives (10E—H) also showed a high activity (ED50=<50 μM), while all of their corresponding isoflavones (8E—I) were not active at all. The 7-hydroxyisoflavanes having either an additional hydroxyl group at the C5-position (9D) or a methoxy group at the C6-position (9J) presented a high activity (ED50=26—32 μM). This study suggests that natural isoflavones have the possibilities of exhibiting antioxidant activities through the hydroxylation at the C6-, C8-, or C3′-position or the formation of the isoflavanes (9) and/or the biphenyl-ketone derivatives (10′) by metabolism or biotransformation.

  合成了四十八种异黄酮（8）、三十一种异黄烷（9）以及四十七种联苯酮（10, 10′），这些化合物是由十一种取代酚（11）和六种苯乙酸（12）合成的。其中，有七十五种化合物是新发现的。这些化合物的自由基清除活性在pH 6.0下使用1,1-二苯基-2-吡唑啉酮（DPPH）进行了评估。我们发现，在四十三种含有儿茶酚基的化合物中，三十九种在A环或B环上表现出与儿茶素相似的高活性（ED50=12—54 μM）。在这些情况下，它们结构的其他部分似乎对活性影响不大。许多6-或8-羟基异黄烷（9E—I）及其联苯酮衍生物（10E—H）也显示出高活性（ED50=<50 μM），而它们对应的异黄酮（8E—I）则完全没有活性。具有在C5位增加羟基（9D）或在C6位增加甲氧基（9J）的7-羟基异黄烷则展现出高活性（ED50=26—32 μM）。本研究表明，天然异黄酮通过在C6、C8或C3′位置的羟基化，或通过代谢或生物转化形成异黄烷（9）和/或联苯酮衍生物（10′），具有表现抗氧化活性的可能性。
• Synthesis, biological evaluation and structure-activity relationship of a novel class of PI3Kα H1047R mutant inhibitors
  作者：Ning Zhang、Zhimei Yu、Xiaohong Yang、Yan Zhou、Jia Wang、Shao-Lin Zhang、Ming-Wei Wang、Yun He

  DOI：10.1016/j.ejmech.2018.09.002

  日期：2018.10

  treatment. As our continuing endeavor to discover isoform and/or mutant selective class of PI3K inhibitors, herein we report the optimization of a structurally novel PI3Kα H1047R mutant inhibitor Hit-02 (EC50 = 115.3 μM), which was identified from a high-throughput screening campaign. Structure-activity relationship analysis enabled us to discover compound 7h, which strongly inhibited PI3Kα H1047R

  磷脂酰肌醇3-激酶α（PI3Kα）是最有吸引力的癌症治疗靶标之一。作为我们不断努力发现PI3K抑制剂的同工型和/或突变体选择性类别的方法，我们在此报告了对结构新颖的PI3KαH1047R突变体抑制剂Hit-02（EC 50  = 115.3μM）的优化，该结构已通过高通量筛选确定活动。结构-活性关系分析使我们能够发现化合物7h，该化合物强烈抑制PI3KαH1047R突变体，其EC 50值为0.55μM ，效力比Hit-02高200倍以上，而对其他PI3K亚型的影响很小。Western blotting检测表明7h降低AKT的磷酸化水平，这是7h抑制PI3KαH1047R突变体功能的另一个证据。细胞活力测定显示7h抑制HCT-116癌细胞的生长，IC 50值为10.9μM。另外，发现7h使细胞周期停滞在G2期，但未显示任何细胞凋亡作用。此外，7h明显诱导细胞自噬，可能有助于其在癌细胞中的抗增
• Benzopyrans and use thereof in treating vascular diseases
  申请人：Zyma SA

  公开号：US04814346A1

  公开（公告）日：1989-03-21

  Isoflavans of the formula I ##STR1## wherein the groups OR, R', R" and ring B are as defined in the specification, exhibit valuable pharmacological properties, especially for the treatment of vascular diseases. They are prepared by methods known per se.

  公式为I ##STR1## 中的异黄酮，其中基团OR、R'、R"和环B的定义如规范中所述，具有有价值的药理特性，特别适用于治疗血管疾病。它们可通过已知的方法制备。
• Bicyclic compounds
  申请人：Zyma SA

  公开号：EP0267155A2

  公开（公告）日：1988-05-11

  Isoflavans of the formula I wherein the groups OR, R', R" and ring B are as defined in the specification, exhibit valueable pharmacological properties, especially for the treatment of vascular diseases. They are prepared by methods known per se.

  式 I 的异黄酮（其中基团 OR、R'、R "和环 B 如说明书中所定义）具有宝贵的药理特性，特别是在治疗血管疾病方面。 它们是通过本身已知的方法制备的。
• Structure–activity relationship studies of flavonoids as potent inhibitors of human platelet 12-hLO, reticulocyte 15-hLO-1, and prostate epithelial 15-hLO-2
  作者：Yesseny Vasquez-Martinez、Rachana V. Ohri、Victor Kenyon、Theodore R. Holman、Silvia Sepúlveda-Boza

  DOI：10.1016/j.bmc.2007.07.036

  日期：2007.12

  Human lipoxygenase (hLO) isozymes have been implicated in a number of disease states and have attracted much attention with respect to their inhibition. One class of inhibitors, the flavonoids, have been shown to be potent lipoxygenase inhibitors but their study has been restricted to those compounds found in nature, which have limited structural variability. We have therefore carried out a comprehensive study to determine the structural requirements for flavonoid potency and selectivity against platelet 12-hLO, reticulocyte 15-hLO-1, and prostate epithelial 15-hLO-2. We conclude from this study that catechols are essential for high potency, that isoflavones and isoflavanones tend to select against 12-hLO, that isoflavans tend to select against 15-hLO-1, but few flavonoids target 15-hLO-2. (C) 2007 Elsevier Ltd. All rights reserved.