8-hydroxy-3-(4-methylphenyl)-coumarin

• 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-methylphenyl)-coumarin
• 英文别名: 8-hydroxy-3-p-tolyl-coumarin；8-Hydroxy-3-p-tolyl-cumarin；8-Hydroxy-3-(4-methylphenyl)chromen-2-one；8-hydroxy-3-(4-methylphenyl)chromen-2-one
• 化学式: C₁₆H₁₂O₃
• 分子量: 252.269
• InChiKey: LIWCBZLCPDYGKB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  对甲基苯乙腈 在 sodium hydroxide 、 吡啶盐酸盐 作用下， 生成 8-hydroxy-3-(4-methylphenyl)-coumarin
  参考文献：
  名称：

  Bz-HYDROXYLATED-3-ARYL- AND 3,4-DIARYL-COUMARINS

  摘要：

  DOI：

  10.1021/jo01374a020

文献信息

• 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.
• Bz-HYDROXYLATED-3-ARYL- AND 3,4-DIARYL-COUMARINS
  作者：NG. PH. BUU-HOÏ、BERNARD EKERT、RENÉ ROYER

  DOI：10.1021/jo01374a020

  日期：1954.9