2'-hydroxy-4-carboxychalcone | 55737-06-9

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: 2'-hydroxy-4-carboxychalcone
• 英文别名: 4-[3-(2-hydroxyphenyl)-3-oxopropenyl]benzoic acid；4-carboxy-2-hydroxy-chalcone；Benzoic acid, 4-[(1E)-3-(2-hydroxyphenyl)-3-oxo-1-propen-1-yl]-；4-[3-(2-hydroxyphenyl)-3-oxoprop-1-enyl]benzoic acid
• CAS: 55737-06-9
• 化学式: C₁₆H₁₂O₄
• 分子量: 268.269
• InChiKey: JOALTNNELYVHQD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  74.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2'-hydroxy-4-carboxychalcone 在 硫酸 、 碘 作用下， 以 二甲基亚砜 为溶剂， 生成 methyl 4-(4-oxo-4H-chromen-2-yl)benzoate
  参考文献：
  名称：

  合成 Chromen-4-One-Oxadiazole 取代类似物作为有效的 β-葡萄糖醛酸酶抑制剂

  摘要：

  Chromen-4-one 取代的恶二唑类似物 1-19 已被合成、表征和评估对 β-葡萄糖醛酸酶的抑制作用。与标准 d-糖精酸 1,4 内酯 (IC50 = 48.1 ± 1.2 μM) 相比，所有类似物都表现出不同程度的 β-葡萄糖醛酸酶抑制活性，IC50 值范围在 0.8 ± 0.1–42.3 ± 0.8 μM 之间。已建立所有化合物的构效关系。进行分子对接研究以预测化合物与酶活性位点的结合相互作用。

  DOI：

  10.3390/molecules24081528
• 作为产物：
  描述：

  2'-羟基苯乙酮 在 potassium hydroxide 、 sodium hydroxide 作用下， 以 甲醇 、 乙醇 、 水 为溶剂， 反应 16.0h， 生成 2'-hydroxy-4-carboxychalcone
  参考文献：
  名称：

  一种查尔酮酰胺类α-葡萄糖苷酶抑制剂及其制备方法与应用

  摘要：

  本发明涉及一种查尔酮酰胺类α‑葡萄糖苷酶抑制剂及其制备与应用，该抑制剂结构式为：#imgabs0#制备方法具体为(1)将2‑羟基苯乙酮，氢氧化钠和对甲酰基苯甲酸甲酯反应后经后处理得到式(a)中间体；(2)取式(a)中间体溶于有机溶剂中和氢氧化钾进行反应，反应后经后处理得到式(b)中间体；(3)取式(b)中间体和取代苯胺溶于有机溶剂中，反应后经后处理得到式(c)所示的抑制剂。与现有技术相比，本发明的化合物结构新颖，实验表明具有良好的α‑葡萄糖苷酶抑制活性，可用于制备抑制α‑葡萄糖苷酶活性的药物。

  公开号：

  CN117430524A

文献信息

• Flavone-based hydrazones as new tyrosinase inhibitors: Synthetic imines with emerging biological potential, SAR, molecular docking and drug-likeness studies
  作者：Reem I. Alsantali、Ehsan Ullah Mughal、Nafeesa Naeem、Meshari A. Alsharif、Amina Sadiq、Anser Ali、Rabab. S. Jassas、Qamar Javed、Asif Javid、Sajjad Hussain Sumrra、Abdulrahman A. Alsimaree、Muhammad Naveed Zafar、Basim H. Asghar、Hatem M. Altass、Ziad Moussa、Saleh A. Ahmed

  DOI：10.1016/j.molstruc.2021.131933

  日期：2022.3

  Ketoconazole. Based on in vitro tyrosinase inhibitory assay, some compounds exhibited potent inhibition particularly, 3g (IC50 = 1.40±0.16 μM), 3j (IC50 = 0.95±0.07 μM), 3o (IC50 = 1.13±0.11 μM), and 3q (IC50 = 1.01±0.1 μM) showed best inhibition i.e., 0.7, 0.5, 0.6 and 0.5 folds, respectively than kojic acid (IC50 = 1.79±0.6 μM). Lineweaver-Burk plots demonstrated that the most potential derivative 3j tyrosinase

  靶向酪氨酸酶 (TYR) 是导致黑色素生成障碍的关键酶，是用于开发黑色素生成抑制剂的众所周知的方法。多种皮肤病和微生物皮肤感染可导致色素沉着过度。因此，探索用于治疗黑色素生成疾病的新支架是一个鼓舞人心的目标。在此背景下，已成功设计、合成和表征了一系列不同取代的黄酮基腙。本研究描述了用于治疗色素沉着过度的新型蘑菇酪氨酸酶抑制剂 (TI) 的发现。在适当的时候，黄酮支架已被纳入对蘑菇酪氨酸酶具有体外抑制作用的新型化学型中，以发现抗黑色素生成剂. 本文制备的类似物的生物学研究表明，对大多数真菌-细菌菌株具有中等至极好的活性，并且它们的活性与市售抗生素（即环丙沙星和酮康唑）的活性相当。基于体外酪氨酸酶抑制试验，一些化合物表现出有效的抑制作用，尤其是3g (IC 50  = 1.40±0.16 μM)、3j (IC 50  = 0.95±0.07 μM)、3o (IC 50  = 1.13±0.11
• Exploring the 2′-Hydroxy-Chalcone Framework for the Development of Dual Antioxidant and Soybean Lipoxygenase Inhibitory Agents
  作者：Ioanna Kostopoulou、Andromachi Tzani、Nestor-Ioannis Polyzos、Maria-Anna Karadendrou、Eftichia Kritsi、Eleni Pontiki、Thalia Liargkova、Dimitra Hadjipavlou-Litina、Panagiotis Zoumpoulakis、Anastasia Detsi

  DOI：10.3390/molecules26092777

  日期：——

  bearing diverse substituents on rings A and B, are presented. Among all the synthesized derivatives, chalcone 4b, bearing two hydroxyl substituents on ring B, was found to possess the best combined activity (82.4% DPPH radical scavenging ability, 82.3% inhibition of lipid peroxidation, and satisfactory LOX inhibition value (IC50 = 70 μM). Chalcone 3c, possessing a methoxymethylene substituent on ring A,

  2'-羟基查尔酮是天然存在的化合物，具有多种生物活性。为了描述有利于抗氧化和脂氧合酶 (LOX) 抑制活性的结构特征，提出了一系列在 A 环和 B 环上带有不同取代基的 2'-羟基查耳酮的设计、合成和生物活性概况。在所有合成的衍生物中，B环上带有两个羟基取代基的查尔酮4b具有最佳的综合活性（DPPH自由基清除能力为82.4%，脂质过氧化抑制率为82.3%，LOX抑制值令人满意（IC 50 = 70） μM），在 A 环上具有甲氧基亚甲基取代基，在 B 环上具有三个甲氧基，表现出最有希望的 LOX 抑制活性（IC 50 = 45 μM）。观察到最活跃的化合物3c及其类似物3b与 LOX A 常见的氢键相互作用模式的关键结合特征，即芳环 A 的羟基和羰基分别朝向 Asp768 和 Asn128。如图3c所示，大的(-OMOM)基团似乎不参与直接结合，但其诱导能够在芳环B的甲氧基与Trp130和Gly247之间形成H键的取向。
• Synthesis and biological evaluation of substituted aurone derivatives as potential tyrosinase inhibitors: <i>in vitro</i>, kinetic, QSAR, docking and drug-likeness studies
  作者：Najla A. Alshaye、Ehsan Ullah Mughal、Eslam B. Elkaeed、Zaman Ashraf、Sana Kehili、Yasir Nazir、Nafeesa Naeem、Nida Abdul Majeed、Amina Sadiq

  DOI：10.1080/07391102.2022.2132296

  日期：——

  synthesized aurone derivatives were found as potent tyrosinase inhibitors relative to the standard kojic acid (IC50 = 16.69 ± 2.81 μM) and the compound 39 inhibited tyrosinase non-competitively (Ki = 11.8 μM) by forming an enzyme-inhibitor complex. The binding modes of these molecules were ascribed through molecular docking studies against tyrosinase protein (PDB ID: 2Y9X). The quantitative structure-activity

  摘要 酪氨酸酶在黑色素生物合成和水果和蔬菜的酶促褐变中起着重要作用。为了发现有效的酪氨酸酶抑制剂，进行了本研究。在此背景下，通过各种光谱技术（包括红外、紫外、 1 H 和13 C-NMR 以及质谱）设计、合成并阐明了合成傲酮衍生物26-50的结构。筛选了目标化合物26-50的抗酪氨酸酶抑制潜力，并通过Lineweaver-Burk图分析了动力学机制。所有目标化合物均表现出良好至优异的 IC 50值，范围为 7.12 ± 0.32 μM 至 66.82 ± 2.44 μM。这些合成的橙酮衍生物被发现是相对于标准曲酸的有效酪氨酸酶抑制剂（IC 50 = 16.69 ± 2.81 μM），并且化合物39通过形成酶抑制剂复合物非竞争性抑制酪氨酸酶（K i = 11.8 μM）。这些分子的结合模式是通过针对酪氨酸酶蛋白（PDB ID：2Y9X）的分子对接研究来确定的。定量构效关系研究显示26-50个结构与其抗酪氨酸酶活性(IC
• Exploring 3-hydroxyflavone scaffolds as mushroom tyrosinase inhibitors: synthesis, X-ray crystallography, antimicrobial, fluorescence behaviour, structure-activity relationship and molecular modelling studies
  作者：Jamshaid Ashraf、Ehsan Ullah Mughal、Amina Sadiq、Maryam Bibi、Nafeesa Naeem、Anser Ali、Anam Massadaq、Nighat Fatima、Asif Javid、Muhammad Naveed Zafar、Bilal Ahmad Khan、Muhammad Faizan Nazar、Amara Mumtaz、Muhammad Nawaz Tahir、Masoud Mirzaei

  DOI：10.1080/07391102.2020.1805364

  日期：2021.12.12

  To explore new scaffolds as tyrosinase enzyme inhibitors remain an interesting goal in the drug discovery and development. In due course and our approach to synthesize bioactive compounds, a series of varyingly substituted 3-hydroxyflavone derivatives (1-23) were synthesized in one-pot reaction and screened forin vitroagainst mushroom tyrosinase enzyme. The structures of newly synthesized compounds were unambiguously corroborated by usual spectroscopic techniques (FTIR, UV-Vis,H-1-,C-13-NMR) and mass spectrometry (EI-MS). The structure of compound15was also characterized by X-ray diffraction analysis. Furthermore, the synthesized compounds (1-23) were evaluated for their antimicrobial potential. Biological studies exhibit pretty good activity against most of the bacterial-fungal strains and their activity is comparable to those of commercially available antibioticsi.e.Cefixime and Clotrimazole. Amongst the series, the compounds2, 4, 5, 6, 7, 10, 11, 14and22exhibited excellent inhibitory activity against tyrosinase, even better than standard compound. Remarkably, the compound2(IC50= 0.280 +/- 0.010 mu g/ml) was found almost sixfold and derivative5(IC50= 0.230 +/- 0.020 mu g/ml) about sevenfold more active as compared to standard Kojic acid (IC50=1.79 +/- 0.6 mu g/ml). Moreover, these synthetic compounds (1-23) displayed good to moderate activities against tested bacterial and fungal strains. Their emission behavior was also investigated in order to know their potential as fluorescent probes. The molecular modelling simulations were also performed to explore their binding interactions with active sites of the tyrosinase enzyme. Limited structure-activity relationship was established to design and develop new tyrosinase inhibitors by employing 2-arylchromone as a structural core in the future. Communicated by Ramaswamy H. Sarma
• Aurones as histone deacetylase inhibitors: Identification of key features
  作者：Vincent Zwick、Alkiviadis-Orfefs Chatzivasileiou、Nathalie Deschamps、Marina Roussaki、Claudia A. Simões-Pires、Alessandra Nurisso、Iza Denis、Christophe Blanquart、Nadine Martinet、Pierre-Alain Carrupt、Anastasia Detsi、Muriel Cuendet

  DOI：10.1016/j.bmcl.2014.10.019

  日期：2014.12

  In this study, a total of 22 flavonoids were tested for their HDAC inhibitory activity using fluorimetric and BRET- based assays. Four aurones were found to be active in both assays and showed IC50 values below 20 mu M in the enzymatic assay. Molecular modelling revealed that the presence of hydroxyl groups was responsible for good compound orientation within the isoenzyme catalytic site and zinc chelation. (C) 2014 Elsevier Ltd. All rights reserved.