6-hydroxy-3-(3’,4’-dihydroxybenzoyl)coumarin | 1456071-21-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 6-hydroxy-3-(3’,4’-dihydroxybenzoyl)coumarin
• 英文别名: 3-(3,4-Dihydroxybenzoyl)-6-hydroxychromen-2-one；3-(3,4-dihydroxybenzoyl)-6-hydroxychromen-2-one
• CAS: 1456071-21-8
• 化学式: C₁₆H₁₀O₆
• 分子量: 298.252
• InChiKey: KGKFQKGDOBAWHC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  104
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  在 三溴化硼 作用下， 以 二氯甲烷 为溶剂， 反应 48.0h， 生成 6-hydroxy-3-(3’,4’-dihydroxybenzoyl)coumarin
  参考文献：
  名称：

  Synthesis of coumarin–chalcone hybrids and evaluation of their antioxidant and trypanocidal properties

  摘要：

  根据对香豆素和查尔酮的生物活性的观察，我们合成了香豆素-查尔酮杂化物，旨在评估其抗氧化性质以及对导致查加斯病的寄生虫克鲁斯锥虫的杀虫活性。尽管所有衍生物在表裂体阶段（克隆Dm28c）的杀虫活性较为温和，但它们被证明是良好的抗氧化剂。基于这些结果，我们可以得出结论，化合物4和5是进行其抗氧化活性体外研究的潜在候选者。这些初步发现鼓励我们未来对这类化合物进行结构优化。

  DOI：

  10.1039/c3md00025g

文献信息

• Adenosine Receptor Ligands: Coumarin–Chalcone Hybrids as Modulating Agents on the Activity of hARs
  作者：Saleta Vazquez-Rodriguez、Santiago Vilar、Sonja Kachler、Karl-Norbert Klotz、Eugenio Uriarte、Fernanda Borges、Maria João Matos

  DOI：10.3390/molecules25184306

  日期：——

  Adenosine receptors (ARs) play an important role in neurological and psychiatric disorders such as Alzheimer’s disease, Parkinson’s disease, epilepsy and schizophrenia. The different subtypes of ARs and the knowledge on their densities and status are important for understanding the mechanisms underlying the pathogenesis of diseases and for developing new therapeutics. Looking for new scaffolds for selective AR ligands, coumarin–chalcone hybrids were synthesized (compounds 1–8) and screened in radioligand binding (hA1, hA2A and hA3) and adenylyl cyclase (hA2B) assays in order to evaluate their affinity for the four human AR subtypes (hARs). Coumarin–chalcone hybrid has been established as a new scaffold suitable for the development of potent and selective ligands for hA1 or hA3 subtypes. In general, hydroxy-substituted hybrids showed some affinity for the hA1, while the methoxy counterparts were selective for the hA3. The most potent hA1 ligand was compound 7 (Ki = 17.7 µM), whereas compound 4 was the most potent ligand for hA3 (Ki = 2.49 µM). In addition, docking studies with hA1 and hA3 homology models were established to analyze the structure–function relationships. Results showed that the different residues located on the protein binding pocket could play an important role in ligand selectivity.

  腺苷受体（ARs）在神经系统和精神疾病如阿尔茨海默病、帕金森病、癫痫和精神分裂症中发挥重要作用。ARs的不同亚型以及对其密度和状态的了解对于理解疾病发病机制并开发新的治疗方法至关重要。为寻找选择性AR配体的新支架，合成了香豆素-香豆素醛杂化物（化合物1-8），并在放射配体结合（hA1、hA2A和hA3）和腺苷酰环化酶（hA2B）测定中进行筛选，以评估它们对四种人类AR亚型（hARs）的亲和力。已经确定香豆素-香豆素醛杂化物作为一种适合开发针对hA1或hA3亚型的有效和选择性配体的新支架。一般来说，羟基取代的杂化物对hA1具有一定的亲和力，而甲氧基对应物对hA3具有选择性。最有效的hA1配体是化合物7（Ki = 17.7 µM），而化合物4是对hA3最有效的配体（Ki = 2.49 µM）。此外，使用hA1和hA3同源模型进行对接研究，分析了结构-功能关系。结果表明，位于蛋白质结合口袋上的不同残基可能在配体的选择性中起重要作用。
• Synthesis of coumarin–chalcone hybrids and evaluation of their antioxidant and trypanocidal properties
  作者：Saleta Vazquez-Rodriguez、Roberto Figueroa-Guíñez、Maria João Matos、Lourdes Santana、Eugenio Uriarte、Michel Lapier、Juan Diego Maya、Claudio Olea-Azar

  DOI：10.1039/c3md00025g

  日期：——

  Based on the observed biological activities of coumarins and chalcones, we have synthesized coumarin–chalcone hybrids with the aim of evaluating their antioxidant properties and trypanocidal activity against Trypanosoma cruzi, the parasite responsible for Chagas disease. All derivatives have been proved to be good antioxidants in spite of their moderate trypanocidal activity in the epimastigote stage (clone Dm28c). Based on these results, we can conclude that compounds 4 and 5 are potential candidates for in vitro studies of their antioxidant activity. These preliminary findings encourage us to the future structural optimization of these kinds of compounds.

  根据对香豆素和查尔酮的生物活性的观察，我们合成了香豆素-查尔酮杂化物，旨在评估其抗氧化性质以及对导致查加斯病的寄生虫克鲁斯锥虫的杀虫活性。尽管所有衍生物在表裂体阶段（克隆Dm28c）的杀虫活性较为温和，但它们被证明是良好的抗氧化剂。基于这些结果，我们可以得出结论，化合物4和5是进行其抗氧化活性体外研究的潜在候选者。这些初步发现鼓励我们未来对这类化合物进行结构优化。