8-hydroxy-3-(4-hydroxyphenyl)-coumarin | 24051-96-5

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 异黄酮类化合物
• 英文名称: 8-hydroxy-3-(4-hydroxyphenyl)-coumarin
• 英文别名: 8-Hydroxy-3-<4-hydroxy-phenyl>-cumarin；8-hydroxy-3-(4-hydroxy-phenyl)-chromen-2-one；8-Hydroxy-3-(4''-hydroxy)phenylcoumarin；8-hydroxy-3-(4-hydroxyphenyl)chromen-2-one
• CAS: 24051-96-5
• 化学式: C₁₅H₁₀O₄
• 分子量: 254.242
• InChiKey: HXOYIYQATHNBKZ-UHFFFAOYSA-N

物化性质

• 熔点：
  237-238 °C
• 沸点：
  520.082±50.00 °C(Press: 760.00 Torr)(predicted)
• 密度：
  1.443±0.06 g/cm3(Temp: 25 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  66.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  8-ethoxy-3-(4'-methoxyphenyl)coumarin 在 氢碘酸 、 乙酸酐 、 溶剂黄146 作用下， 反应 3.0h， 以61%的产率得到8-hydroxy-3-(4-hydroxyphenyl)-coumarin
  参考文献：
  名称：

  New halogenated phenylcoumarins as tyrosinase inhibitors

  摘要：

  With the aim to find out structural features for the tyrosinase inhibitory activity, in the present communication we report the synthesis and pharmacological evaluation of a new series of phenylcoumarin derivatives with different number of hydroxyl or ether groups and bromo substituent in the scaffold. The synthesized compounds 5-12 were evaluated as mushroom tyrosinase inhibitors showing, two of them, lower IC50 than the umbelliferone. Compound 12 (IC50 = 215 mu M) is the best tyrosinase inhibitor of this series. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.04.012

文献信息

• Synthesis and biological evaluation of 3-arylcoumarins as potential anti-Alzheimer's disease agents
  作者：Jie Yang、Pingping Zhang、Yuheng Hu、Teng Liu、Jie Sun、Xiaojing Wang

  DOI：10.1080/14756366.2019.1574297

  日期：2019.1.1

  the extremely complex pathogenesis. Accumulating evidence indicates there is a close relationship between several enzymes and Alzheimer's disease. Various substituted 3-arylcoumarin derivatives were synthesised, and their in vitro activity, including cholinesterase inhibitory activity, monoamine oxidase inhibitory activity, and antioxidant activity were investigated. Most of the compounds exhibited

  抽象的 阿尔茨海默氏病是一种神经退行性疾病，其发病机理极为复杂。越来越多的证据表明，几种酶与阿尔茨海默氏病之间存在密切的关系。合成了各种取代的3-芳基香豆素衍生物，并研究了它们的体外活性，包括胆碱酯酶抑制活性，单胺氧化酶抑制活性和抗氧化活性。大多数化合物表现出高活性。因此3-芳基香豆素类化合物具有治疗阿尔茨海默氏病的潜力。
• Synthesis and biological evaluation of 3-arylcoumarin derivatives as potential anti-diabetic agents
  作者：Yuheng Hu、Bing Wang、Jie Yang、Teng Liu、Jie Sun、Xiaojing Wang

  DOI：10.1080/14756366.2018.1518958

  日期：2019.1.1

  Abstract A variety of substituted 3-arylcoumarin derivatives were synthesised through microwave radiation heating. The method has characteristics of environmental friendliness, economy, simple separation, and purification process, less by-products and high reaction yield. Those 3-arylcoumarin derivatives were screened for antioxidant, α-glucosidase inhibitory and advanced glycation end-products (AGEs)

  抽象的 通过微波辐射加热合成了多种取代的3-芳基香豆素衍生物。该方法具有环境友好，经济，分离纯化工艺简单，副产物少，反应收率高的特点。筛选了那些3-芳基香豆素衍生物的抗氧化剂，α-葡萄糖苷酶抑制物和晚期糖基化终产物（AGEs）形成抑制物。大多数化合物表现出显着的抗氧化剂和AGEs形成抑制活性。抗糖尿病活性研究表明，化合物11和17在体内与标准药物glibenclamide等效。根据实验结果，目标化合物35可用作开发抗糖尿病新药的先导化合物。整个实验表明，抗糖尿病活性在3-芳基香豆素中普遍存在，为抗糖尿病活性药物的开发增加了新的天然骨架。
• Remarkable antioxidant properties of a series of hydroxy-3-arylcoumarins
  作者：Maria João Matos、Fernanda Pérez-Cruz、Saleta Vazquez-Rodriguez、Eugenio Uriarte、Lourdes Santana、Fernanda Borges、Claudio Olea-Azar

  DOI：10.1016/j.bmc.2013.04.015

  日期：2013.7

  In the present work we synthesized a series of hydroxy-3-arylcoumarins (compounds 1-9), some of them previously described as MAO-B selective inhibitors, with the aim of evaluating their antioxidant properties. Theoretical evaluation of ADME properties of all the derivatives was also carried. out. From the ORAC-FL, ESR and CV data it was concluded that these derivatives are very good antioxidants, with a very interesting hydroxyl, DPPH and superoxide radicals scavenging profiles. In particular compound 9 is the most active and effective antioxidant of the series (ORAC-FL = 13.5, capacity of scavenging hydroxyl radicals = 100%, capacity of scavenging DPPH radicals = 65.9% and capacity of scavenging superoxide radicals = 71.5%). Kinetics profile for protection fluorescein probe against peroxyl radicals by addition of antioxidant molecule 9 was also performed. Therefore, it can operate as a potential candidate for preventing or minimizing the free radicals overproduction in oxidative-stress related diseases. (C) 2013 The Authors. Published by Elsevier Ltd. All rights reserved.
• [EN] CANCER METASTASIS INHIBITOR<br/>[FR] INHIBITEUR DE MÉTASTASES CANCÉREUSES<br/>[JA] 癌転移抑制剤
  申请人：KYOTO PHARMACEUTICAL UNIV

  公开号：WO2020130120A1

  公开（公告）日：2020-06-25

  本発明は、新規な癌転移抑制剤に関する。本発明によれば、式（Ｉ）： [式中の各記号の定義は、明細書に記載の通りである。] で表される化合物、又はその医薬上許容される塩を有効成分として含有することを特徴とする癌転移抑制剤を提供することができる。
• New halogenated phenylcoumarins as tyrosinase inhibitors
  作者：Maria João Matos、Lourdes Santana、Eugenio Uriarte、Giovanna Delogu、Marcella Corda、Maria Benedetta Fadda、Benedetta Era、Antonella Fais

  DOI：10.1016/j.bmcl.2011.04.012

  日期：2011.6

  With the aim to find out structural features for the tyrosinase inhibitory activity, in the present communication we report the synthesis and pharmacological evaluation of a new series of phenylcoumarin derivatives with different number of hydroxyl or ether groups and bromo substituent in the scaffold. The synthesized compounds 5-12 were evaluated as mushroom tyrosinase inhibitors showing, two of them, lower IC50 than the umbelliferone. Compound 12 (IC50 = 215 mu M) is the best tyrosinase inhibitor of this series. (C) 2011 Elsevier Ltd. All rights reserved.