1-(2,4-二羟基苯基)-2-(4-硝基苯基)-乙酮 | 15485-63-9

• 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-(4-硝基苯基)-乙酮
• 中文别名: 2,4-二羟基-4'-硝基去氧安息香
• 英文名称: 1,4-Dihydroxyphenyl 4-nitrobenzyl ketone
• 英文别名: 2,4-dihydroxy-4'-nitrodeoxybenzoin；1-(2,4-dihydroxyphenyl)-2-(4-nitrophenyl)ethanone；4'-Nitro-2,4-dihydroxy-desoxybenzoin；2,4-Dihydroxy-4'-nitro-desoxybenzoin
• CAS: 15485-63-9
• 化学式: C₁₄H₁₁NO₅
• 分子量: 273.245
• InChiKey: OGFAWKRXZLGJSK-UHFFFAOYSA-N

物化性质

• 熔点：
  2210°C
• 沸点：
  523.6±19.0 °C(Predicted)
• 密度：
  1.435±0.06 g/cm3(Predicted)
• 溶解度：
  >41 [ug/mL]

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  20
• 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：
  103
• 氢给体数：
  2
• 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-(4-硝基苯基)-乙酮 在 吗啉 、 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 、 异丙醇 为溶剂， 反应 11.0h， 生成 7-O-ethoxycarbonylpentyl-4'-nitroisoflavone
  参考文献：
  名称：

  Synthesis of daidzin analogues as potential agents for alcohol abuse

  摘要：

  Daidzin, the active principle of an herbal remedy for 'alcohol addiction', has been shown to reduce alcohol consumption in all laboratory animals tested to date. Correlation studies using structural analogues of daidzin suggests that it acts by raising the monoamine oxidase (MAO)/mitochondrial aldehyde dehydrogenase (ALDH-2) activity ratio (J. Med. Chem. 2000, 43, 4169). Structure-activity relationship (SAR) studies on the 7-O-substituted analogues of daidzin have revealed structural features important for ALDH-2 and MAO inhibition (J. Med. Chem. 2001, 44, 3320). We here evaluated effects of substitutions at 2, 5, 6, 8, 3' and 4' positions of daidzin on its potencies for ALDH-2 and MAO inhibition. Results show that analogues with 4'-substituents that are small, polar and with hydrogen bonding capacities are most potent ALDH-2 inhibitors, whereas those that are non-polar and with electron withdrawing capacities are potent MAO inhibitors. Analogues with a 5-OH group are less potent ALDH-2 inhibitors but are more potent MAO inhibitors. All the 2-, 6-, 8- and 3'-substituted analogues tested so far do not inhibit ALDH-2 and/or have decreased potencies for MAO inhibition. This, together with the results obtained from previous studies, suggests that a potent antidipsotropic analogue would be a 4',7-disubstituted isoflavone. The 4'-substituent should be small, polar, and with hydrogen bonding capacities such as, -OH and -NH2; whereas the 7-substituent should be a straight-chain alkyl with a terminal polar function such as -(CH2)(n)-OH with 2 less than or equal to n less than or equal to 6, -(CH2)(n)-COOH with 5 less than or equal to n less than or equal to 10, or -(CH2)(n)-NH2 with n greater than or equal to 4. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(03)00397-3
• 作为产物：
  描述：

  对硝基苯乙腈 在 盐酸 、 水 、 zinc(II) chloride 作用下， 以 乙醚 为溶剂， 反应 1.0h， 生成 1-(2,4-二羟基苯基)-2-(4-硝基苯基)-乙酮
  参考文献：
  名称：

  新型大豆苷元类似物和天冬氨酸体外抗流感活性

  摘要：

  基于中药（TCM）活性成分黄豆苷元的结构修饰合成了一系列新型异黄酮，并在体外评估了它们在MDCK细胞中对抗H1N1达菲耐药（H1N1 TR）病毒的抗流感活性线。其中，4-oxo-4H-1-benzopyran-8-carbaldehydes 11a-11g 是最有前途的，它们表现出与核苷类抗病毒剂利巴利文相比更好的活性和选择性。3-(4-Bromophenyl)-7-hydroxy-4-oxo-4H-1-benzopyran-8-carboxaldehyde (11c) 显示出最好的抑制活性 (EC50, 29.0 μM) 和选择性指数 (SI>10.3)。

  DOI：

  10.1002/cbdv.201400337

文献信息

• Synthesis and Properties of 2-Carboxyethyland 2-Carboxypropylchromones
  作者：G. P. Mrug、B. A. Demidchuk、S. P. Bondarenko、N. V. Gorbulenko、M. S. Frasinyuk

  DOI：10.1007/s10600-019-02710-x

  日期：2019.5

  Reaction features of polyhydroxydeoxybenzoins and their heteroatomic analogs with succinic and glutaric anhydrides were studied and shown to be useful for synthesizing 3-(3-pyrazolyl)butyric acids and 4,11-dioxo-8,10,11,12-tetrahydro-4H,9H-pyrano[2,3-a]xanthene derivatives with a butyric acid moiety.

  研究了聚羟基脱氧安息香及其杂原子类似物与琥珀酸和戊二酸酐的反应特征，并证明可用于合成 3-(3-吡唑基)丁酸和 4,11-dioxo-8,10,11,12-四氢-4H，具有丁酸部分的 9H-吡喃并[2,3-a]呫吨衍生物。
• 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
• Structure-guided design and synthesis of isoflavone analogs of GW4064 with potent lipid accumulation inhibitory activities
  作者：Rongmao Qiu、Guoshun Luo、Xuerong Cai、Linyi Liu、Mingqi Chen、Deying Chen、Qidong You、Hua Xiang

  DOI：10.1016/j.bmcl.2018.10.021

  日期：2018.12

  reported a series of isoflavone derivatives with antidyslipidemic activity. With this background, a series of isoflavone analogs of GW4064 were designed, synthesized and evaluated the lipid-lowering activity of analogs. As a result, most of compounds significantly reduced the lipid accumulation in 3T3-L1 adipocytes and four of them (10a, 11, 15c and 15d) showed stronger inhibitory than GW4064. The most

  我们的小组先前已经报道了一系列具有抗血脂异常活性的异黄酮衍生物。在此背景下，设计，合成并评估了一系列GW4064的异黄酮类似物。其结果是，大多数化合物的显著降低脂质积聚在3T3-L1脂肪细胞和它们（四个10A，11，15C和15D）显示出比GW4064抑制更强。最有效的化合物15d在基于细胞的萤光素酶报告基因检测中表现出对FXR的有希望的激动活性。同时15d上调FXR，SHP和BSEP基因表达，下调脂肪生成基因SREBP-1c的mRNA表达。此外，与GW4064相比，在HepG2细胞毒性试验中还观察到了15d的改进安全性。分子对接研究进一步证实了获得的生物学结果，结果表明15d很好地适合FXR的结合口袋，并同时与一些关键残基相互作用。
• <i>In Vitro</i>Study of Isoflavones and Isoflavans as Potent Inhibitors of Human 12- and 15-Lipoxygenases
  作者：Carolina Mascayano、Victoria Espinosa、Silvia Sepúlveda-Boza、Eric K. Hoobler、Steve Perry

  DOI：10.1111/cbdd.12157

  日期：2013.9

  In this study, we have investigated 16 isoflavone and isoflavan derivatives as potential inhibitors of human lipoxygenase (platelet 12‐lipoxygenase, reticulocyte 15‐lipoxygenase‐1, and epithelial 15‐lipoxygenase‐2). The flavonoid baicalein, a known lipoxygenase inhibitor, was used as positive control. Four compounds, 6,7‐dihydroxy‐3′‐chloroisoflavone (1c), 7‐hydroxy‐8‐methyl‐4′‐chloroisoflavan (5a)

  在这项研究中，我们研究了16种异黄酮和异黄酮衍生物作为人类脂氧合酶的潜在抑制剂（血小板12-脂氧合酶，网状细胞15-脂氧合酶-1和上皮15-脂氧合酶-2）。类黄酮黄ical素（一种已知的脂加氧酶抑制剂）用作阳性对照。四种化合物，6,7-二羟基-3'-氯异黄酮（1c），7-羟基-8-甲基-4'-氯异黄酮（5a），7,8-二羟基-4'-甲基异黄酮（5b）和7， 8-dihydroxy-3'methylisoflavan（5c）是有效的12-lipoxygenases和15-lipoxygenase-1的抑制剂，IC 50小于10μm，而6,7-dihydroxy-4-4'-nitroisoflavone（1b）是12-脂氧合酶的选择性抑制剂。对三种最佳抑制剂（1b，5b，5c）进行了对接研究，抗氧化剂测定和动力学测量。结果表明，环A中的邻苯二酚基团对于这些化合物的抗氧化性能至关重要，并且可能对
• A facile and practical preparation of 5,7-dihydroxy-3-(4-nitrophenyl)-4<i>H</i>-1-benzopyran-4-one
  作者：D. F. Liu、C. C. Cheng

  DOI：10.1002/jhet.5570280632

  日期：1991.10

  methods for the synthesis of hydroxylated isoflavones were reported during the past fifty years, none is suitable for the preparation of isoflavones containing 5,7-dihydroxyl functions. This paper reports a simple, large scale preparation of 5,7-dihydroxy-3-(4-nitrophenyl)-4H-1-benzopyran-4-one (2a) by the condensation of the readily available 4-nitrobenzyl 2,4,6-trihydroxyphenyl ketone (1a) and acetic-formic

  尽管在过去的五十年中已经报道了几种合成方法来合成羟基化的异黄酮，但没有一种方法适合于制备具有5,7-二羟基官能团的异黄酮。本文报告了一种简单的大规模制备5,7-二羟基-3-（4-硝基苯基）-4 H -1-苯并吡喃-4-酮（2a）的方法，该方法是通过将现成的4-硝基苄基2,4缩合1,6-三羟苯基酮（1a）和乙甲酸酐的收率很高。类似异黄酮，如7-羟基-3-（4-硝基苯基）-4- ħ -1-苯并吡喃-4-酮（2B）也可在类似的方式良好的产率获得。