2′,4-dihydroxy-3-methoxychalcone | 25205-49-6

• 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′,4-dihydroxy-3-methoxychalcone
• 英文别名: 3-(4-hydroxy-3-methoxyphenyl)-1-(2-hydroxyphenyl)prop-2-en-1-one
• CAS: 25205-49-6
• 化学式: C₁₆H₁₄O₄
• 分子量: 270.285
• InChiKey: NGQQEEYHKPKSER-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  66.8
• 氢给体数：
  2
• 氢受体数：
  4

安全信息

• 海关编码：
  2914509090

反应信息

• 作为反应物：
  描述：

  2′,4-dihydroxy-3-methoxychalcone 在 碘 作用下， 以 二甲基亚砜 为溶剂， 反应 1.0h， 生成 2-(4-羟基-3-甲氧基苯基)-4H-色烯-4-酮
  参考文献：
  名称：

  Design, synthesis and biological activity of flavonoid derivatives as selective agonists for neuromedin U 2 receptor

  摘要：

  Central neuromedin U 2 receptor (NMU2R) plays important roles in the regulation of food intake and body weight. Identification of NMU2R agonists may lead to the development of pharmaceutical agents to treat obesity. Based on the structure of rutin, a typical flavonoid and one of the NMU2R agonists we previously identified from an in-house made natural product library, 30 flavonoid derivatives have been synthesized and screened on a cell-based reporter gene assay. A number of compounds were found to be selective and highly potent to NMU2R. For example, the EC50 value of compound NRA 4 is very close to that of NMU, the endogenous peptide ligand of NMU2R. Structure-activity relationship analysis revealed that a 3-hydroxyl group in ring C and a 2'-fluoride group in ring B were essential for this class of compounds to be active against NMU2R. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2014.08.038
• 作为产物：
  描述：

  2'-羟基苯乙酮 、 香草醛 在 sodium hydroxide 作用下， 生成 2′,4-dihydroxy-3-methoxychalcone
  参考文献：
  名称：

  Glycolytic Inhibition and Antidiabetic Activity on Synthesized Flavanone Scaffolds with Computer Aided Drug Designing Tools

  摘要：

  背景：糖尿病是一种具有挑战性的代谢紊乱，当HbA1c水平未得到控制时会导致一系列并发症。市场上现有的大部分长期使用的药物可能会导致严重的不良反应。因此，当前的研究重点在于通过合成天然模拟类黄酮类似物来开发治疗糖尿病的药物。 目标：本研究侧重于合成模拟天然类黄酮核心的黄酮衍生物，并对其抗糖尿病和抗氧化活性进行研究，这有助于开发针对糖尿病管理的药物发现。 材料和方法：从1,3-二苯基-丙-2-烯-1-酮衍生物合成了新型的2-苯基-2,3-二氢-香豆素，并利用紫外线、红外线、核磁共振、质谱等技术对其进行表征。通过图论分析确定了药物靶点位点，并通过对其物理化学性质、ADMET研究和分子对接分析进行了体外研究。通过体外（α-淀粉酶抑制实验）和体内模型研究了抗糖尿病和自由基清除效果。利用链脲霉素（STZ）诱导的大鼠作为体内模型。 结果：α-淀粉酶抑制实验显示，具有羟基取代的黄酮类物质HFA1-HFA7具有显著的IC50值。将试验化合物（HFA3-HFA7）以40 mg/kg剂量用于STZ诱导的大鼠，发现HFA5、HFA4和HFA6等具有电子给予基团（如羟基、甲氧基和硫苯基）的化合物明显恢复了血糖水平和抗氧化酶活性，与格列本脲相比。 结论：这些结果表明，天然模拟合成的黄酮类物质具有抗糖尿病和抗氧化性能，有助于开发针对糖尿病管理的药物。

  DOI：

  10.2174/1570180817999201209204523

文献信息

• The Synthesis and Evaluation of Novel Hydroxyl Substituted Chalcone Analogs with in Vitro Anti-Free Radicals Pharmacological Activity and in Vivo Anti-Oxidation Activity in a Free Radical-Injury Alzheimer’s Model
  作者：Ying Pan、Yicun Chen、Qingnan Li、Xiaoyu Yu、Jinzhi Wang、Jinhong Zheng

  DOI：10.3390/molecules18021693

  日期：——

  Alzheimer’s disease (AD) pathogenesis involves an imbalance between free radical formation and destruction. In order to obtain a novel preclinical anti-AD drug candidate, we synthesized a series of novel hydroxyl chalcone analogs which possessed anti-free radical activity, and screened their effects on scavenging 2,2-diphenyl-1-picrylhydrazyl (DPPH) and OH free radicals in vitro. Compound C7, 4,2'-dihydroxy-3,5-dimethoxychalcone was found to have potent activity in these anti-free radical activity tests. Further research revealed that C7 could elevate glutathione peroxidase (GSH-PX) and super oxide dismutase (SOD) levels and lower malonaldehyde (MDA) level in vivo in the Alzheimer’s model. The indication of C7’s effect on AD needs further study.

  阿尔茨海默病（AD）的发病机制涉及自由基形成与消耗之间的失衡。为了获得一种新型的临床前抗阿尔茨海默病药物候选物，我们合成了一系列新型氢氧基查尔酮类似物，这些化合物具有抗自由基活性，并筛选了它们在体外清除2,2-二苯基-1-苦味酰肼（DPPH）和羟基自由基的效果。化合物C7，4,2'-二羟基-3,5-二甲氧基查尔酮，在这些抗自由基活性测试中表现出强效活性。进一步研究显示，C7能够在阿尔茨海默模型中提高过氧化氢酶（GSH-PX）和超氧化物歧化酶（SOD）水平，并降低丙二醛（MDA）水平。C7对阿尔茨海默病的作用指示需要进一步研究。
• Synthesis and evaluation of novel carbamate-substituted flavanone derivatives as potent acetylcholinesterase inhibitors and anti-amnestic agents
  作者：Preet Anand、Baldev Singh

  DOI：10.1007/s00044-012-0162-3

  日期：2013.4

  This study was designed to synthesize and evaluate flavanone derivatives with phenylcarbamate moiety as potent acetylcholinesterase (AChE) inhibitors and anti-amnestic agents for management of AD. The synthesis of carbamate-substituted flavanone derivatives involved base-catalysed Claisen-Schmidt condensation reaction of 2-hydroxy acetophenone/2-hydroxy-4,6-dimethoxyacetophenone with differently substituted

  本研究旨在合成和评估具有氨基甲酸酯部分的黄烷酮衍生物，作为有效的乙酰胆碱酯酶（AChE）抑制剂和抗记忆删除剂，用于治疗AD。氨基甲酸酯取代的黄烷酮衍生物的合成涉及2-羟基苯乙酮/ 2-羟基-4,6-二甲氧基苯乙酮与不同取代的苯甲醛的碱催化的Claisen-Schmidt缩合反应，以产生不同取代的查耳酮，其在回流时经历分子内氧化环化用冰醋酸制得黄烷酮化合物。此后，在石油醚和三乙胺存在下，将黄烷酮化合物与异氰酸苯酯回流，得到苯基氨基甲酸酯取代的黄烷酮衍生物。以多奈哌齐为标准药物，体外筛选合成的化合物对AChE的抑制活性。最有效的测试化合物通过Morris水迷宫测试，评价了（5f '）在体内东pol碱（0.4mg / kg）引起的健忘症中的记忆恢复作用。所有化合物均显示出对AChE的抑制活性，其中氨基甲酸酯取代的5,7-二甲氧基黄烷酮衍生物（5a' - 5g '）是最有效的化合物，IC 50为21
• USE OF 4-HYDROXYDIHYDROCHALCONES AND THEIR SALTS FOR ENHANCING AN IMPRESSION OF SWEETNESS
  申请人：Krammer Gerhard

  公开号：US20100233102A1

  公开（公告）日：2010-09-16

  The invention provides the use of a 4-hydroxydihydrochalcone of the formula (I) wherein R 1 , R 2 , R 3 and R 4 each, independently, represent H, OH or O-alkyl, with the proviso that at least one of the groups R 1 , R 2 or R 3 represents OH, a salt of such a 4-hydroxydihydrochalcone of the formula (I), a mixture containing or consisting of two or more different 4-hydroxydihydrochalcones of the formula (I), wherein R 1 , R 2 , R 3 and R 4 are each defined in the way given above, a mixture containing or consisting of salts of two or more different 4-hydroxydihydrochalcones of the formula (I), wherein R 1 , R 2 , R 3 and R 4 are each defined in the way given above or a mixture containing or consisting of a 4-hydroxydihydrochalcone of the formula (I) or two or more different 4-hydroxydihydrochalcones of the formula (I), wherein R 1 , R 2 , R 3 and R 4 are each defined in the way given above, and a salt of a 4-hydroxydihydrochalcone of the formula (I) or two or more salts of different 4-hydroxydihydrochalcones of the formula (I), wherein R 1 , R 2 , R 3 and R 4 are each defined in the way given above, to enhance the sweet taste of a sweet-tasting substance or the impression of a sweet smell of a flavouring that gives an impression of a sweet smell.

  本发明提供使用式(I)的4-羟基二氢查尔酮，其中R1、R2、R3和R4各自独立地表示H、OH或O-烷基，但至少其中一个基团R1、R2或R3表示OH，以及该式(I)的4-羟基二氢查尔酮的盐，含有或由两种或更多不同的式(I)的4-羟基二氢查尔酮混合而成，其中R1、R2、R3和R4的定义如上所述，含有或由两种或更多不同的式(I)的4-羟基二氢查尔酮的盐混合而成，其中R1、R2、R3和R4的定义如上所述，含有或由式(I)的4-羟基二氢查尔酮或两种或更多不同的式(I)的4-羟基二氢查尔酮混合而成，其中R1、R2、R3和R4的定义如上所述，以及式(I)的4-羟基二氢查尔酮的盐或两种或更多不同的式(I)的4-羟基二氢查尔酮的盐混合而成，用于增强甜味物质的甜味或给予甜味香料的甜味印象。
• Use of 4-hydroxydihydrochalcones and their salts for enhancing an impression of sweetness
  申请人：Krammer Gerhard

  公开号：US09445606B2

  公开（公告）日：2016-09-20

  The invention provides the use of a 4-hydroxydihydrochalcone of the formula (I) wherein R1, R2, R3 and R4 each, independently, represent H, OH or O-alkyl, with the proviso that at least one of the groups R1, R2 or R3 represents OH, a salt of such a 4-hydroxydihydrochalcone of the formula (I), a mixture containing or consisting of two or more different 4-hydroxydihydrochalcones of the formula (I), wherein R1, R2, R3 and R4 are each defined in the way given above, a mixture containing or consisting of salts of two or more different 4-hydroxydihydrochalcones of the formula (I), wherein R1, R2, R3 and R4 are each defined in the way given above or a mixture containing or consisting of a 4-hydroxydihydrochalcone of the formula (I) or two or more different 4-hydroxydihydrochalcones of the formula (I), wherein R1, R2, R3 and R4 are each defined in the way given above, and a salt of a 4-hydroxydihydrochalcone of the formula (I) or two or more salts of different 4-hydroxydihydrochalcones of the formula (I), wherein R1, R2, R3 and R4 are each defined in the way given above, to enhance the sweet taste of a sweet-tasting substance or the impression of a sweet smell of a flavoring that gives an impression of a sweet smell.

  本发明提供了使用式(I)的4-羟基二氢查尔酮，其中R1、R2、R3和R4各自独立地表示H、OH或O-烷基，但至少其中一个基团R1、R2或R3表示OH，以及该式(I)的这样的4-羟基二氢查尔酮的盐，含有或由两种或两种以上不同的式(I)的4-羟基二氢查尔酮混合而成，其中R1、R2、R3和R4的定义如上所述，含有或由两种或两种以上不同的式(I)的4-羟基二氢查尔酮的盐混合而成，其中R1、R2、R3和R4的定义如上所述，或含有或由式(I)的4-羟基二氢查尔酮或两种或两种以上不同的式(I)的4-羟基二氢查尔酮混合而成，其中R1、R2、R3和R4的定义如上所述，以及式(I)的4-羟基二氢查尔酮的盐或两种或两种以上不同的式(I)的4-羟基二氢查尔酮的盐混合而成，用于增强甜味物质的甜味或给予甜味香料的印象。
• Design, synthesis and MAO inhibitory activity of 2-(arylmethylidene)-2,3-dihydro-1-benzofuran-3-one derivatives
  作者：Vishnu Nayak Badavath、Chandrani Nath、Narayana Murthy Ganta、Gulberk Ucar、Barij Nayan Sinha、Venkatesan Jayaprakash

  DOI：10.1016/j.cclet.2017.02.009

  日期：2017.7

  A series of 2-(arylmethylidene)-2,3-dihydro-1-benzofuran-3-one derivatives (aurones, 1-20) were synthesized and screened for their inhibitory activity against hMAO. Seventeen compounds (1-5, 7-17, 19) were found to be selective towards hMAO-B, while two were non -selective (6 and 20) and one (18) selective towards hMAO-A. Compound 17 (Ki = 0.10 +/- 0.01 mu mol/L) was found to be equally potent and selective towards hMAO-B, when compared with the standard drug Selegiline (Ki = 0.12 0.01 p.mol/L). Nature and position of substitution in aryl ring at 2nd position of benzofuranone influences hMAO-B inhibitory potency, while their structural bulkiness influences selectivity between hMAO-A and hMAO-B. Molecular docking simulation was also carried out to understand the interaction of inhibitor with the enzyme at molecular level, and we found the docking results were in good agreement with the experimental values. Comparison of the activity profile of the aurones with their corresponding flavones reported earlier by our group revealed that there exists no difference in potency as well as selectivity. (C) 2017 Chinese Chemical Society and Institute of Materia Medica, Chinese Academy of Medical Sciences. Published by Elsevier B.V. All rights reserved.