[1-(2,4-二羟基苯基)-2-(3’,4’-二羟基苯基)乙酮 | 887354-66-7

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 中文名称: [1-(2,4-二羟基苯基)-2-(3’,4’-二羟基苯基)乙酮
• 英文名称: 1-(2,4-dihydroxyphenyl)-2-(3',4'-dihydroxyphenyl)ethanone
• 英文别名: 1-(2,4-dihydroxyphenyl)-2-(3,4-dihydroxyphenyl)ethanone
• CAS: 887354-66-7
• 化学式: C₁₄H₁₂O₅
• 分子量: 260.246
• InChiKey: HYSCQSOORVAXEH-UHFFFAOYSA-N

物化性质

• 熔点：
  210-212°C
• 沸点：
  554.9±40.0 °C(Predicted)
• 密度：
  1.483±0.06 g/cm3(Predicted)
• 溶解度：
  可溶于DMSO（少量）、乙酸乙酯、甲醇（少量）

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  98
• 氢给体数：
  4
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  [1-(2,4-二羟基苯基)-2-(3’,4’-二羟基苯基)乙酮 在 三氟化硼乙醚 、 potassium carbonate 作用下， 以 氯仿 、 N,N-二甲基甲酰胺 为溶剂， 反应 19.0h， 生成 3',4'-7-Trihydroxyisoflavontriacetat
  参考文献：
  名称：

  作为胰腺脂肪酶抑制剂的天然异黄酮和半合成衍生物

  摘要：

  肥胖症现在在世界各地普遍存在，经常与一些慢性疾病有关。因此，人们对肥胖症的预防和治疗越来越感兴趣。迄今为止，唯一的抗肥胖药物是奥利司他，这是一种天然产物衍生的胰脂肪酶 (PL) 抑制剂，具有一些不良副作用。在过去的几十年中，许多天然化合物或衍生物已被评估为潜在的 PL 抑制剂，而天然多酚是最有希望作为抗肥胖剂开发的。然而，很少有研究致力于异黄酮。在这项工作中，我们报告了一个小型半合成异黄酮衍生物文库以及天然先导黄豆苷元 ( 1 )、染料木素 ( 2 ) 和芒柄花素 ( 2 )的 PL 抑制特性研究。3）。体外脂肪酶抑制试验表明，2是最有前途的 PL 抑制剂。在合成异黄酮中，羟基化和溴化衍生物比它们的天然先导物更有效。通过荧光测量和脂肪酶抑制动力学的详细研究表明，2和溴代衍生物10和11对 PL 具有最大的亲和力。对接研究证实了这些发现，突出了异黄酮和酶之间的相互作用，证实羟基化和溴化是有用的修饰。

  DOI：

  10.1021/acs.jnatprod.0c01387
• 作为产物：
  描述：

  3,4-二羟基苯乙酸 、 间苯二酚 在 三氟化硼乙醚 作用下， 反应 2.0h， 生成 [1-(2,4-二羟基苯基)-2-(3’,4’-二羟基苯基)乙酮
  参考文献：
  名称：

  Development of 3-alkyl-6-methoxy-7-hydroxy-chromones (AMHCs) from natural isoflavones, a new class of fluorescent scaffolds for biological imaging

  摘要：

  一种新型荧光物质3-烷基-6-甲氧基-7-羟基-香豆素（AMHCs）已开发，并适用于生物成像试剂。

  DOI：

  10.1039/c4cc06762b

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。
• Isoflavone metabolites
  申请人：Joannou Eustace George

  公开号：US20050222248A1

  公开（公告）日：2005-10-06

  There are disclosed compounds of formulae (I) or (II) in which A is selected from the group consisting of (1), (2), (3) and (4);OH, and one of R 1 and R 2 is selected from H, OH and OCH 3 , and the other of R 1 and R 2 is selected from OH and OCH 3 ; one of R3 and R4 is selected from H, OH and OCH3, and the other of R3 and R4 is selected from OH and OCH3; provided that at least one of the pairs R 1 , R 2 and R 3 , R 4 are both OH; R 5 is selected from OH and OCH 3 ; and ------ denotes a single or double bond; and pharmaceutically acceptable salts and prodrugs thereof. The compounds of the invention are useful for the treatment of hormone-dependent conditions and cancers.

  在公式（I）或（II）中披露了化合物，其中A选自以下组合：（1）、（2）、（3）和（4）；OH，R1和R2中的一个选自H、OH和OCH3，另一个选自OH和OCH3；R3和R4中的一个选自H、OH和OCH3，另一个选自OH和OCH3；前提是R1、R2和R3、R4中至少有一对是OH；R5选自OH和OCH3；以及------表示单键或双键；以及其药学上可接受的盐和前药。该发明的化合物对于治疗激素依赖性疾病和癌症是有用的。
• ISOFLAVONE METABOLITES
  申请人：Joannou George Eustace

  公开号：US20080125481A1

  公开（公告）日：2008-05-29

  There are disclosed compounds of formulae (I) or (II) in which A is selected from the group consisting of (1), (2), (3) and (4); OH, and one of R 1 and R 2 is selected from H, OH and OCH 3 , and the other of R 1 and R 2 is selected from OH and OCH 3 ; one of R3 and R4 is selected from H, OH and OCH3, and the other of R3 and R4 is selected from OH and OCH3; provided that at least one of the pairs R 1 , R 2 and R 3 , R 4 are both OH; R 5 is selected from OH and OCH 3 ; and denotes a single or double bond; and pharmaceutically acceptable salts and prodrugs thereof. The compounds of the invention are useful for the treatment of hormone-dependent conditions and cancers.

  公开了式（I）或（II）的化合物，其中A从（1），（2），（3）和（4）组成的群体中选择；OH，R1和R2中的一个选择自H，OH和OCH3，另一个选择自OH和OCH3；R3和R4中的一个选择自H，OH和OCH3，另一个选择自OH和OCH3；前提是R1，R2和R3，R4中至少有一对是OH；R5选择自OH和OCH3；并表示单键或双键；以及其药学上可接受的盐和前药。本发明的化合物用于治疗激素依赖性疾病和癌症。
• The effectiveness of synthetic methoxylated isoflavones in delivering to the skin and alleviating psoriasiform lesions via topical absorption
  作者：Chih-Hua Tseng、Chwan-Fwu Lin、Ibrahim A. Aljuffali、Jhao-Rong Huang、Sien-Hung Yang、Jia-You Fang

  DOI：10.1016/j.ijpharm.2022.121629

  日期：2022.4
• Preparation, characterizations and anti-pollutant activity of 7,3&amp;prime;,4&amp;prime;-trihydroxyisoflavone nanoparticles in particulate matter-induced HaCaT keratinocytes
  作者：Pao-Hsien Huang、Chih-Hua Tseng、Chia-Yu Lin、Chiang-Wen Lee、Feng-Lin Yen

  DOI：10.2147/ijn.s153323

  日期：——

  Background: 7,3',4'-Trihydroxyisoflavone (734THI), a secondary metabolite derived from daidzein in soybean, possesses several biological activities, including antioxidant, skin whitening and anti-atopic dermatitis properties, but the poor aqueous solubility of 734THI has limited its application in medicine and cosmetic industry.Methods: The aim of the present study was to improve the physicochemical properties of 734THI using planetary ball mill preparation under a solvent-free process to improve its solubility and anti-pollutant activity.Results: 734THI nanoparticle powder (734THIN) was successfully prepared by the planetary ball mill technique using polyvinylpyrrolidone K30 as the excipient. 734THIN effectively increased the aqueous solubility and cellular uptake of 734THI by improving its physicochemical properties, including particle size reduction, crystalline-amorphous transformation and intermolecular hydrogen bonding with polyvinylpyrrolidone K30. In addition, 734THIN inhibited the overexpression of COX-2 and MMP-9 by downregulating MAPK pathway signaling in particulate matter-exposed HaCaT keratinocytes, while raw 734THI in PBS with low aqueous solubility did not show any anti-inflammatory or antiaging activity.Conclusion: 734THIN may be used as an additive in anti-pollutant skin care products for preventing particulate matter-induced inflammation and aging in skin.