2,3,4,4'-tetrahydroxydeoxybenzoin | 77316-95-1

• 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: 2,3,4,4'-tetrahydroxydeoxybenzoin
• 英文别名: 2-(4-hydroxyphenyl)-1-(2,3,4-trihydroxyphenyl)ethanone
• CAS: 77316-95-1
• 化学式: C₁₄H₁₂O₅
• 分子量: 260.246
• InChiKey: MPGPMJNRPGWFKC-UHFFFAOYSA-N

物化性质

• 熔点：
  208–209°C

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：

  2,3,4,4'-tetrahydroxydeoxybenzoin 在 甲基磺酰氯 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 以83%的产率得到7,8-二羟基-3-(4-羟基苯基)苯并吡喃-4-酮
  参考文献：
  名称：

  Waehaelae, Kristiina; Hase, Tapio A., Journal of the Chemical Society. Perkin transactions I, 1991, # 12, p. 3005 - 3008

  摘要：

  DOI：
• 作为产物：
  描述：

  对羟基苯乙腈 在 盐酸 、 水 、 zinc(II) chloride 作用下， 以 乙醚 为溶剂， 生成 2,3,4,4'-tetrahydroxydeoxybenzoin
  参考文献：
  名称：

  Enzymatic Studies of Isoflavonoids as Selective and Potent Inhibitors of Human Leukocyte 5-Lipo-Oxygenase

  摘要：

  Continuing our search to find more potent and selective 5‐LOX inhibitors, we present now the enzymatic evaluation of seventeen isoflavones (IR) and nine isoflavans (HIR), and their in vitro and in cellulo potency against human leukocyte 5‐LOX. Of the 26 compounds tested, 10 isoflavones and 9 isoflavans possessed micromolar potency, but only three were selective against 5‐LOX (IR‐2, HIR‐303, and HIR‐309), with IC50 values at least 10 times lower than those of 12‐LOX, 15‐LOX‐1, and 15‐LOX‐2. Of these three, IR‐2 (6,7‐dihydroxy‐4‐methoxy‐isoflavone, known as texasin) was the most selective 5‐LOX inhibitor, with over 80‐fold potency difference compared with other isozymes; Steered Molecular Dynamics (SMD) studies supported these findings. The presence of the catechol group on ring A (6,7‐dihydroxy versus 7,8‐dihydroxy) correlated with their biological activity, but the reduction of ring C, converting the isoflavones to isoflavans, and the substituent positions on ring B did not affect their potency against 5‐LOX. Two of the most potent/selective inhibitors (HIR‐303 and HIR‐309) were reductive inhibitors and were potent against 5‐LOX in human whole blood, indicating that isoflavans can be potent and selective inhibitors against human leukocyte 5‐LOX in vitro and in cellulo.

  DOI：

  10.1111/cbdd.12469

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
• 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
• The synthesis, structure and activity evaluation of pyrogallol and catechol derivatives as Helicobacter pylori urease inhibitors
  作者：Zhu-Ping Xiao、Tao-Wu Ma、Wei-Chang Fu、Xiao-Chun Peng、Ai-Hua Zhang、Hai-Liang Zhu

  DOI：10.1016/j.ejmech.2010.08.015

  日期：2010.11

  Some pyrogallol and catechol derivatives were synthesized, and their urease inhibitory activity was evaluated by using acetohydroxamic acid (AHA), a well known Helicobacter pylori urease inhibitor, as positive control. The assay results indicate that many compounds have showed potential inhibitory activity against H. pylori urease. 4-(4-Hydroxyphenethyl)phen-1,2-diol (2a) was found to be the most potent

  合成了一些邻苯三酚和邻苯二酚衍生物，并使用众所周知的幽门螺杆菌脲酶抑制剂乙酰氧肟酸（AHA）作为阳性对照，评估了它们对脲酶的抑制活性。测定结果表明许多化合物已显示出对幽门螺杆菌脲酶的潜在抑制活性。已发现4-（4-羟基苯乙基）phen-1,2-二醇（2a）是最有效的脲酶抑制剂，提取分数的IC 50值为1.5±0.2μM，完整细胞的IC 50值为4.2±0.3μM，至少10分别比AHA低2倍和20倍（IC 50为17.2±0.9μM，100.6±13μM）。这一发现表明2a潜在的脲酶抑制剂将值得进一步研究。为了理解所观察到的良好活性，进行了2a到幽门螺杆菌脲酶活性位点的分子对接。
• Development of 3-alkyl-6-methoxy-7-hydroxy-chromones (AMHCs) from natural isoflavones, a new class of fluorescent scaffolds for biological imaging
  作者：Jianzhuang Miao、Huaqing Cui、Jing Jin、Fangfang Lai、Hui Wen、Xiang Zhang、Gian Filippo Ruda、Xiaoguang Chen、Dali Yin

  DOI：10.1039/c4cc06762b

  日期：——

  A new class of fluorophores 3-alkyl-6-methoxy-7-hydroxy-chromones (AMHCs) is developed and is suitable as reagents for biological imaging.

  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。
• 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。