(E)-5-hydroxy-2-(2-(thiophen-2-yl)vinyl)-4H-pyran-4-one | 1334399-78-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃
• 英文名称: (E)-5-hydroxy-2-(2-(thiophen-2-yl)vinyl)-4H-pyran-4-one
• CAS: 1334399-78-8
• 化学式: C₁₁H₈O₃S
• 分子量: 220.249
• InChiKey: OZRFHCVACMIOGU-ONEGZZNKSA-N

物化性质

• 沸点：
  451.9±45.0 °C(predicted)
• 密度：
  1.560±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.58
• 重原子数：
  15.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  50.44
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为产物：
  描述：

  (E)-5-(4-methoxybenzyloxy)-2-(2-(thiophen-2-yl)vinyl)-4H-pyran-4-one 在 三溴化硼 、 甲醇 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 以54%的产率得到(E)-5-hydroxy-2-(2-(thiophen-2-yl)vinyl)-4H-pyran-4-one
  参考文献：
  名称：

  Synthesis of Pyronyl Derivatives as Resveratrol Analogues and Their Inhibitory Effects on Nitric Oxide and PGE₂Productions

  摘要：

  DOI：

  10.5012/bkcs.2011.32.1.299

文献信息

• Resveratrol–Maltol and Resveratrol–Thiophene Hybrids as Cholinesterase Inhibitors and Antioxidants: Synthesis, Biometal Chelating Capability and Crystal Structure
  作者：Milena Mlakić、Lajos Fodor、Ilijana Odak、Ottó Horváth、Marija Jelena Lovrić、Danijela Barić、Valentina Milašinović、Krešimir Molčanov、Željko Marinić、Zlata Lasić、Irena Škorić

  DOI：10.3390/molecules27196379

  日期：——

  New resveratrol–thiophene and resveratrol–maltol hybrids were synthesized as cholinesterase inhibitors and antioxidants. As with photostability experiments, biological tests also found remarkable differences in the properties and behavior of thiophene and maltol hybrids. While resveratrol–thiophene hybrids have excellent inhibitory and antioxidant properties (similar to the activity of reference drug galantamine), maltols have been proven to be weaker inhibitors and antioxidants. The molecular docking of selected active ligands gave insight into the structures of docked enzymes. It enabled the identification of interactions between the ligand and the active site of both cholinesterases. The maltols that proved to be active cholinesterase inhibitors were able to coordinate Fe3+ ion, forming complexes of 1:1 composition. Their formation constants, determined by spectrophotometry, are very similar, lgK = 11.6–12.6, suggesting that Fe3+ binds to the common hydroxy-pyranone moiety and is hardly affected by the other aromatic part of the ligand. Accordingly, the characteristic bands in their individual absorption spectra are uniformly red-shifted relative to those of the free ligands. The crystal structures of two new resveratrol–maltol hybrids were recorded, giving additional information on the molecules’ intermolecular hydrogen bonds and packing. In this way, several functionalities of these new resveratrol hybrids were examined as a necessary approach to finding more effective drugs for complicated neurodegenerative diseases.

  新的白藜芦醇-噻吩和白藜芦醇-麦芽酚杂化物被合成为胆碱酯酶抑制剂和抗氧化剂。与光稳定性实验一样，生物测试也发现了噻吩和麦芽酚杂化物的性质和行为方面的显著差异。虽然白藜芦醇-噻吩杂化物具有出色的抑制和抗氧化性能（类似于参考药物加兰他敏的活性），但已证明麦芽酚是较弱的抑制剂和抗氧化剂。所选活性配体的分子对接揭示了对接酶的结构。它使得识别配体与胆碱酯酶的活性位点之间的相互作用成为可能。已证明为活性胆碱酯酶抑制剂的麦芽酚能够配位Fe3+离子，形成1:1组成的配合物。通过分光光度法确定的它们的形成常数非常相似，lgK = 11.6-12.6，表明Fe3+离子结合到共同的羟基吡喃酮部分，几乎不受配体的其他芳香部分的影响。因此，它们各自的吸收光谱中的特征带相对于游离配体均匀地向红移。记录了两个新的白藜芦醇-麦芽酚杂化物的晶体结构，提供了有关分子间氢键和包装的额外信息。通过这种方式，检查了这些新白藜芦醇杂化物的几个功能，作为寻找更有效的药物治疗复杂神经退行性疾病的必要方法。