2,3,4-trihydroxydesoxybenzoin | 22761-00-8

• 物质功能分类: 医药中间体 - 原料药中间体
• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: 2,3,4-trihydroxydesoxybenzoin
• 英文别名: 2-Phenyl-1-(2,3,4-trihydroxyphenyl)ethanone
• CAS: 22761-00-8
• 化学式: C₁₄H₁₂O₄
• 分子量: 244.247
• InChiKey: YYKGZYGSFFMVEP-UHFFFAOYSA-N

物化性质

• 熔点：
  141–142°C

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  18
• 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：
  77.8
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2,3,4-trihydroxydesoxybenzoin 生成 benzyl 2,3,4-trimethoxyphenyl ketone
  参考文献：
  名称：

  JAIN, A. C.;PALIWAL, POONAM, INDIAN J. CHEM. B, 27,(1988) N1, C. 985-988

  摘要：

  DOI：
• 作为产物：
  描述：

  在 盐酸 作用下， 生成 2,3,4-trihydroxydesoxybenzoin
  参考文献：
  名称：

  Structure–activity relationship studies of flavonoids as potent inhibitors of human platelet 12-hLO, reticulocyte 15-hLO-1, and prostate epithelial 15-hLO-2

  摘要：

  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.

  DOI：

  10.1016/j.bmc.2007.07.036

文献信息

• Discovery and Development of Small-Molecule Inhibitors of Glycogen Synthase
  作者：Buyun Tang、Mykhaylo S. Frasinyuk、Vimbai M. Chikwana、Krishna K. Mahalingan、Cynthia A. Morgan、Dyann M. Segvich、Svitlana P. Bondarenko、Galyna P. Mrug、Przemyslaw Wyrebek、David S. Watt、Anna A. DePaoli-Roach、Peter J. Roach、Thomas D. Hurley

  DOI：10.1021/acs.jmedchem.9b01851

  日期：2020.4.9

  at 2.85 Å, as well as kinetic data, revealed that H23 bound within the uridine diphosphate glucose binding pocket of yGsy2p. The high conservation of residues between human and yeast GS in direct contact with H23 informed the development of around 500 H23 analogs. These analogs produced a structure-activity relationship profile that led to the identification of a substituted pyrazole, 4-(4-(4-hydro

  糖原的过度积累是各种糖原贮积病（GSD）的标志，包括庞贝病，科里病，安徒生病和拉福拉病。越来越多的证据表明，抑制糖原累积代表了治疗这些GSD的潜在治疗方法。使用设计用于筛选关键糖原合成酶，糖原合成酶（GS）抑制剂的荧光偏振分析，我们确定了取代的咪唑（rac）-2-甲氧基-4-（1-（2-（1-（1-甲基吡咯烷酮- （2-基）乙基）-4-苯基-1H-咪唑-5-基）苯酚（H23），是酵母GS 2（yGsy2p）的首批抑制剂。来自X射线晶体学在2.85Å处的数据以及动力学数据表明，H23结合在yGsy2p的尿苷二磷酸葡萄糖结合口袋中。直接与H23接触的人与酵母GS之间残基的高度保守性有助于开发约500种H23类似物。这些类似物产生了结构-活性关系图，从而鉴定了取代的吡唑4-（4-（4-羟苯基）-3-（三氟甲基）-1H-吡唑-5-基）邻苯三酚和300-对人GS的效力提高了两倍。这些取代的吡唑具有有
• A Concise Approach to Oxo-Dehydrorotenoid by Direct Lactonization and the Total Syntheses of Stemonone, Rotenonone, 6-Oxo-dehydroelliptone, and 6-Oxo-6a,12a-dehydrodeguelin
  作者：Jutatip Boonsombat、Sanit Thongnest、Somsak Ruchirawat

  DOI：10.1002/ejoc.201900078

  日期：2019.5.26

  An approach to construct the oxo‐dehydrorotenoids via direct lactonization of isoflavone‐2‐carboxylic acids is reported. The application of this method for the first total syntheses of the natural products, stemonone, 6‐oxo‐dehydroelliptone, rotenonone, and 6‐oxo‐6a,12a‐dehydrodeguelin, are demonstrated. The series of oxo‐dehydrorotenoids was also evaluated for their biological activities.

  据报道，有一种通过异黄酮2-羧酸直接内酯化来构建羰基-脱氢类胡萝卜素的方法。演示了该方法在天然产物首次合成中的应用，该合成物为马酮酮，6-氧代-脱氢Elliptone，鱼藤酮和6-氧代-6a，12a-脱氢deguelin。还评估了一系列氧-脱氢类胡萝卜素的生物活性。
• Free-Radical-Scavenging, Antityrosinase, and Cellular Melanogenesis Inhibitory Activities of Synthetic Isoflavones
  作者：Tzy-Ming Lu、Horng-Huey Ko、Lean-Teik Ng、Yen-Pin Hsieh

  DOI：10.1002/cbdv.201400208

  日期：2015.6

  potential of synthetic isoflavones for application in cosmeceuticals. Twenty‐five isoflavones were synthesized and their capacities of free‐radical‐scavenging and mushroom tyrosinase inhibition, as well as their impact on cell viability of B16F10 murine melanoma cells and HaCaT human keratinocytes were evaluated. Isoflavones that showed significant mushroom tyrosinase inhibitory activities were further

  在这项研究中，我们研究了合成异黄酮在药妆品中的应用潜力。合成了 25 种异黄酮，并评估了它们清除自由基和抑制蘑菇酪氨酸酶的能力，以及它们对 B16F10 鼠黑色素瘤细胞和 HaCaT 人角质形成细胞的细胞活力的影响。进一步研究了显示出显着蘑菇酪氨酸酶抑制活性的异黄酮在体外 B16F10 黑素细胞中减少细胞黑色素形成和抗酪氨酸酶活性。在测试的异黄酮中，6-羟基黄豆苷元 (2) 是 ABTS.+ 和 DPPH 的最强清除剂。SC50 值分别为 11.3±0.3 和 9.4±0.1 μM 的自由基。Texasin (20) 表现出最有效的蘑菇酪氨酸酶抑制作用 (IC50 14.9±4.5 μM)，而 retusin (17) 分别显示出对 B16F10 黑素细胞中细胞黑色素形成和抗酪氨酸酶活性的最有效抑制。总之，retusin (17) 和 texasin (20) 都表现出强大的自由基清除能力
• 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。
• Discovery of Novel 2′,3′,4′-Trihydroxy-2-phenylacetophenone Derivatives as Anti-Gram-Positive Antibacterial Agents
  作者：Hideyuki GOTO、Yuji KUMADA、Hitoshi ASHIDA、Ken-ichi YOSHIDA

  DOI：10.1271/bbb.80532

  日期：2009.1.23

  A number of 2′,3′,4′-trihydroxy-2-phenylacetophenone derivatives were synthesized and examined for growth inhibition of several kinds of bacteria. 2′,3′,4′-Trihydroxy-2-phenylacetophenone itself exhibited no antibacterial activity, but some of its derivatives showed various antibacterial activities depending on functional groups introduced on the 2-phenyl ring. Eighteen out of 24 compounds synthesized in this study appeared to possess antibacterial activities against at least two Gram-positive strains of Bacillus subtilis and Staphylococcus aureus, 2-(biphenyl-4-yl)-2′,3′,4′-trihydroxyacetophenone being the most active with LC50 of 5.8 μm and 5.6 μm respectively. However, none of the synthesized compounds exhibited inhibitory effects on Gram-negative strains, such as Escherichia coli, Proteus mirabilis, Pseudomonas aeruginosa, and Salmonella enterica, suggesting that anti-Gram-positive specificity of the antibacterial compounds.

  研究人员合成了一些 2′,3′,4′-三羟基-2-苯基苯乙酮衍生物，并考察了它们对几种细菌生长的抑制作用。2′,3′,4′-三羟基-2-苯基苯乙酮本身没有抗菌活性，但它的一些衍生物根据在 2-苯基环上引入的官能团的不同而表现出不同的抗菌活性。在本研究合成的 24 种化合物中，有 18 种似乎对至少两种革兰氏阳性菌株枯草杆菌和金黄色葡萄球菌具有抗菌活性，其中 2-（联苯-4-基）-2′,3′,4′-三羟基苯乙酮的活性最高，半数致死浓度分别为 5.8 μm 和 5.6 μm。然而，合成的化合物均未对革兰氏阴性菌株（如大肠杆菌、变形杆菌、铜绿假单胞菌和肠炎沙门氏菌）产生抑制作用，这表明这些抗菌化合物具有抗革兰氏阳性菌的特异性。