7-allyloxynaringenin | 1416850-04-8

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 黄酮类化合物
• 英文名称: 7-allyloxynaringenin
• 英文别名: 7-allyloxy-4′,5-dihydroxyflavanone；5-Hydroxy-2-(4-hydroxyphenyl)-7-prop-2-enoxy-2,3-dihydrochromen-4-one；5-hydroxy-2-(4-hydroxyphenyl)-7-prop-2-enoxy-2,3-dihydrochromen-4-one
• CAS: 1416850-04-8
• 化学式: C₁₈H₁₆O₅
• 分子量: 312.322
• InChiKey: YXRHKNYHUXTYGW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  76
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  7-allyloxynaringenin 在 N-氯代丁二酰亚胺 、 palladium 10% on activated carbon 、 氢气 作用下， 以 四氯化碳 、 乙醇 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 180.0 ℃ 、101.33 kPa 条件下， 反应 25.0h， 生成 8-chloro-2,3-dihydro-5,7-dihydroxy-2-(4-hydroxyphenyl)-6-propylchromen-4-one
  参考文献：
  名称：

  6,8-SUBSTITUTED NARINGENIN DERIVATIVE AND USE THEREOF

  摘要：

  本发明公开了一种6,8-取代的柚皮素衍生物，如式（I）所示：其中，式（I）中的A6和A8分别选自H、卤素、羟基、含1-3个碳原子的烷基、直链烯基、醇基、醛基或含2-3个碳原子的羧酸基，通过对柚皮素进行改性而得到，或其药学上可接受的盐，其制备方法以及用于制备改善呼吸系统功能和缓解咳嗽药物的用途。

  公开号：

  US20160130245A1
• 作为产物：
  描述：

  diallyl sulfate 、 (S)-柚皮素 在 potassium carbonate 作用下， 以 丙酮 为溶剂， 以58%的产率得到7-allyloxynaringenin
  参考文献：
  名称：

  Synthesis and Evaluation of the Acetylcholinesterase Inhibitory Activities of Some Flavonoids Derived from Naringenin

  摘要：

  阿尔茨海默病（AD）是一种不可逆的神经退行性疾病，严重影响许多老年人。随着人口老龄化，AD已经给许多发达国家的医疗保健系统带来了巨大的社会经济负担。现在非常需要新的治疗方法来阻止或逆转疾病的进展。一种在寻找AD新治疗方法上引起科学家长期关注的研究方法是通过抑制乙酰胆碱酯酶（AChE）来重新建立胆碱能传递。柚皮素是一种具有潜在抑制AChE活性的类黄酮。从柚皮素中可以合成许多其他类黄酮衍生物，如类黄酮和香豆素。本研究采用Williamson方法合成了九种类黄酮衍生物，包括四种类黄酮和五种香豆素。通过Ellman方法评估AChE抑制活性，发现有四种物质（2、4、5和7）具有相对较好的生物活性（IC50 <100μM），这些生物活性比柚皮素更好。分子对接揭示了与催化三联体氨基酸残基Ser200和酶的周围区域的强相互作用对于强烈的AChE抑制效果至关重要。化合物7具有最强的AChE抑制活性（IC50 13.0 ± 1.9μM）。这种物质可以用于进一步的研究。

  DOI：

  10.1155/2021/4817900

文献信息

• Design, synthesis and inhibitory activities of naringenin derivatives on human colon cancer cells
  作者：Hyuk Yoon、Tae Woo Kim、Soon Young Shin、Mi Joo Park、Yeonjoong Yong、Dong Woon Kim、Tasneem Islam、Young Han Lee、Kang-Yeoun Jung、Yoongho Lim

  DOI：10.1016/j.bmcl.2012.10.130

  日期：2013.1

  Based on the previous result, several naringenin derivatives modified at position 7 with bulky substituents were designed and synthesized, and their inhibitory effects on HCT116 human colon cancer cells were tested using a clonogenic assay. The half maximal inhibitory concentrations (IC50) of five naringenin derivatives ranged between 1.20 mu M and 20.01 mu M which are much better than naringenin used as a control. In addition, new structural modification at C-4 of flavanone results in improving both the anti-cancer effect and anti-oxidative effect. In vitro cyclin dependent kinase 2 (CDK2) binding assay was carried out based on the previous results. To elucidate the possible interaction between naringenin derivatives and CDK2, in silico docking study was performed. This result demonstrates the rationale for the different inhibitory activities of the naringenin derivatives. These findings could be used for designing cancer therapeutic or preventive flavanone-derived agents. (c) 2012 Elsevier Ltd. All rights reserved.
• Synthesis and Evaluation of the Acetylcholinesterase Inhibitory Activities of Some Flavonoids Derived from Naringenin
  作者：The-Huan Tran、Thi-Thu-Hien Vo、Thi-Quynh-Nhi Vo、Thi-Cam-Nhung Cao、Thai-Son Tran

  DOI：10.1155/2021/4817900

  日期：2021.11.30

  Alzheimer’s disease (AD) is an irreversible neurodegenerative disease that affects many older people adversely. AD has been putting a huge socioeconomic burden on the healthcare systems of many developed countries with aging populations. The need for new therapies that can halt or reverse the progression of the disease is now extremely great. A research approach in the finding new treatment for AD that has attracted much interest from scientists for a long time is the reestablishment of cholinergic transmission through inhibition of acetylcholinesterase (AChE). Naringenin is a flavonoid with the potential inhibitory activity against AChE. From naringenin, many other flavonoid derivatives, such as flavanones and chalcones, can be synthesized. In this study, by applying the Williamson method, nine flavonoid derivatives were synthesized, including four flavanones and five chalcones. The evaluation of AChE inhibitory activity by the Ellman method showed that there were four substances (2, 4, 5, and 7) with relatively good biological activities (IC50 < 100 μM), and these biological activities were better than that of naringenin. The molecular docking revealed that strong interactions with amino acid residue Ser200 of the catalytic triad and those of the peripheral region of the enzyme were crucial for strong effects against AChE. Compound 7 had the strongest AChE inhibitory activity (IC50 13.0 ± 1.9 μM). This substance could be used for further studies.

  阿尔茨海默病（AD）是一种不可逆的神经退行性疾病，严重影响许多老年人。随着人口老龄化，AD已经给许多发达国家的医疗保健系统带来了巨大的社会经济负担。现在非常需要新的治疗方法来阻止或逆转疾病的进展。一种在寻找AD新治疗方法上引起科学家长期关注的研究方法是通过抑制乙酰胆碱酯酶（AChE）来重新建立胆碱能传递。柚皮素是一种具有潜在抑制AChE活性的类黄酮。从柚皮素中可以合成许多其他类黄酮衍生物，如类黄酮和香豆素。本研究采用Williamson方法合成了九种类黄酮衍生物，包括四种类黄酮和五种香豆素。通过Ellman方法评估AChE抑制活性，发现有四种物质（2、4、5和7）具有相对较好的生物活性（IC50 <100μM），这些生物活性比柚皮素更好。分子对接揭示了与催化三联体氨基酸残基Ser200和酶的周围区域的强相互作用对于强烈的AChE抑制效果至关重要。化合物7具有最强的AChE抑制活性（IC50 13.0 ± 1.9μM）。这种物质可以用于进一步的研究。
• 6,8-SUBSTITUTED NARINGENIN DERIVATIVE AND USE THEREOF
  申请人：SU Weiwei

  公开号：US20160130245A1

  公开（公告）日：2016-05-12

  Disclosed in the present invention are a 6,8-substituted naringenin derivative as shown in formula (I): in which A 6 and A 8 in formula (I) are respectively selected from H, halogen, hydroxyl, an alkyl group with 1-3 carbon atoms, and a straight-chain alkenyl, alcohol group, aldehyde group, or carboxylic acid group containing 2-3 carbon atoms, obtained by modifying naringenin as lead compound, or a pharmaceutically acceptable salt thereof, a preparation method therefor and use thereof in preparation of drugs for improving the function of the respiratory system and relieving cough.

  本发明公开了一种6,8-取代的柚皮素衍生物，如式（I）所示：其中，式（I）中的A6和A8分别选自H、卤素、羟基、含1-3个碳原子的烷基、直链烯基、醇基、醛基或含2-3个碳原子的羧酸基，通过对柚皮素进行改性而得到，或其药学上可接受的盐，其制备方法以及用于制备改善呼吸系统功能和缓解咳嗽药物的用途。