6,8-dihydroxy-3-(3,5-dihydroxyphenyl)coumarin | 873869-57-9

• 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: 6,8-dihydroxy-3-(3,5-dihydroxyphenyl)coumarin
• 英文别名: 3-(3,5-Dihydroxyphenyl)-6,8-dihydroxy-2H-1-benzopyran-2-one；3-(3,5-dihydroxyphenyl)-6,8-dihydroxychromen-2-one
• CAS: 873869-57-9
• 化学式: C₁₅H₁₀O₆
• 分子量: 286.241
• InChiKey: UTRZVEMCMITTIW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  21
• 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：
  107
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  2-hydroxy-3,5-dimethoxybenzaldehyde 在 氢碘酸 、 乙酸酐 、 溶剂黄146 、 N,N'-二环己基碳二亚胺 作用下， 以 二甲基亚砜 为溶剂， 反应 15.0h， 生成 6,8-dihydroxy-3-(3,5-dihydroxyphenyl)coumarin
  参考文献：
  名称：

  Design, synthesis, and vasorelaxant and platelet antiaggregatory activities of coumarin–resveratrol hybrids

  摘要：

  We have synthesized the coumarin-resveratrol hybrid 4 and its dimethoxy derivative 3 by a very direct synthetic route involving a Pechmann procedure. Compound 4 has also been synthesized by an alternative route (Perkin), which also allowed the synthesis of compounds 9-13. In addition, we have evaluated the potential vasorelaxant activity of the new compounds in endothelium-containing rat aorta rings pre-contracted with noradrenaline, as well as the inhibitory effects on platelet aggregation induced by thrombin in washed human platelets. The compounds reported here relaxed vascular smooth muscle and inhibited platelet aggregation with a profile similar to that of trans-resveratrol (t-RESV) and, in some cases, showed activity higher than that of the natural compound. This is the case for compound 13, which has a vasorelaxant activity that is twice as high as that of t-resveratrol and a platelet antiaggregant activity that is six times higher. These results suggest that these novel compounds may have potential as structural templates for the design and subsequent development of new vasodilatory and platelet antiaggregatory drugs. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.10.013

文献信息

• Tyrosinase Inhibitor Activity of Coumarin-Resveratrol Hybrids
  作者：Antonella Fais、Marcella Corda、Benedetta Era、M. Benedetta Fadda、Maria Joao Matos、Elias Quezada q、Lourdes Santana、Carmen Picciau、Gianni Podda、Giovanna Delogu

  DOI：10.3390/molecules14072514

  日期：——

  In the present work we report on the contribution of the coumarin moiety to tyrosinase inhibition. Coumarin-resveratrol hybrids 1-8 have been resynthesized to investigate the structure-activity relationships and the IC50 values of these compounds were measured. The results showed that these compounds exhibited tyrosinase inhibitory activity. Compound 3-(3’,4’,5’-trihydroxyphenyl)-6,8-dihydroxycoumarin (8)is the most potentcompound (0.27 mM), more so than umbelliferone (0.42 mM), used as reference compound. The kinetic studies revealed that compound 8 caused non-competitive tyrosinase inhibition.

  在本研究中，我们报告了香豆素分子对酪氨酸酶抑制作用的贡献。我们重新合成了香豆素-白藜芦醇混合物 1-8，以研究其结构-活性关系，并测定了这些化合物的 IC50 值。结果表明，这些化合物具有抑制酪氨酸酶的活性。化合物 3-(3',4',5'-三羟基苯基)-6,8-二羟基香豆素（8）是最有效的化合物（0.27 mM），比作为参考化合物的伞形酮（0.42 mM）更有效。动力学研究表明，化合物 8 对酪氨酸酶具有非竞争性抑制作用。
• Design, synthesis, and vasorelaxant and platelet antiaggregatory activities of coumarin–resveratrol hybrids
  作者：Santiago Vilar、Elías Quezada、Lourdes Santana、Eugenio Uriarte、Matilde Yánez、Nuria Fraiz、Carlos Alcaide、Ernesto Cano、Francisco Orallo

  DOI：10.1016/j.bmcl.2005.10.013

  日期：2006.1

  We have synthesized the coumarin-resveratrol hybrid 4 and its dimethoxy derivative 3 by a very direct synthetic route involving a Pechmann procedure. Compound 4 has also been synthesized by an alternative route (Perkin), which also allowed the synthesis of compounds 9-13. In addition, we have evaluated the potential vasorelaxant activity of the new compounds in endothelium-containing rat aorta rings pre-contracted with noradrenaline, as well as the inhibitory effects on platelet aggregation induced by thrombin in washed human platelets. The compounds reported here relaxed vascular smooth muscle and inhibited platelet aggregation with a profile similar to that of trans-resveratrol (t-RESV) and, in some cases, showed activity higher than that of the natural compound. This is the case for compound 13, which has a vasorelaxant activity that is twice as high as that of t-resveratrol and a platelet antiaggregant activity that is six times higher. These results suggest that these novel compounds may have potential as structural templates for the design and subsequent development of new vasodilatory and platelet antiaggregatory drugs. (c) 2005 Elsevier Ltd. All rights reserved.