(2R,3R,4R,4aS,5R,10aR)-2-hydroxymethyl-5-methoxy-7-methyl-2,3,4,4a,5,10a-hexahydropyrano[2,3-b]chromen-3,4-diol | 1336840-03-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: (2R,3R,4R,4aS,5R,10aR)-2-hydroxymethyl-5-methoxy-7-methyl-2,3,4,4a,5,10a-hexahydropyrano[2,3-b]chromen-3,4-diol
• 英文别名: (2R,3R,4R,4aS,5R,10aR)-2-hydroxymethyl-5-methoxy-7-methyl-2,3,4,4a,5,10a-hexahydropyrano[2,3-b]chromene-3,4-diol；(2R,3R,4R,4aS,5R,10aR)-2-(hydroxymethyl)-7-methyl-5-methoxy-2,3,4,4a,5,10a-hexahydropyran[2,3-b]chromene-3,4-diol；(2R,3R,4R,4aS,5R,10aR)-2-(hydroxymethyl)-5-methoxy-7-methyl-2,3,4,4a,5,10a-hexahydropyrano[2,3-b]chromene-3,4-diol
• CAS: 1336840-03-9
• 化学式: C₁₅H₂₀O₆
• 分子量: 296.32
• InChiKey: AHUNCBIUUDEKJJ-GHRCFYLDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  88.4
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (2R,3R,4R,4aS,5R,10aR)-2-hydroxymethyl-5-methoxy-7-methyl-2,3,4,4a,5,10a-hexahydropyrano[2,3-b]chromen-3,4-diol 、 溴乙酰溴 在 2,4,6-三甲基吡啶 作用下， 以 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 0.67h， 以54%的产率得到((2R,3R,4R,4aS,5R,10aR)-3,4-dihydroxy-5-methoxy-7-methyl-2,3,4,4a,5,10a-hexahydropyrano[2,3-b]chromen-2-yl)methyl 2-bromoacetate
  参考文献：
  名称：

  Nanoliposomes presenting on surface a cis-glycofused benzopyran compound display binding affinity and aggregation inhibition ability towards Amyloid β1-42 peptide

  摘要：

  Nanoliposomes decorated on their surface with ligands for A beta-peptides, the key morphological features of Alzheimer's disease (AD), have been synthesized and characterized for their ability to target A beta-peptide aggregates. A tricyclic benzopyrane-glycofused structure has been exploited as A beta-peptide ligand, which was linked to liposomes via a copper-free, chemoselective, biocompatible click chemistry reaction. The tricyclic-decorated liposomes presented a mean diameter in the nanomolar range (150-200 nm), a negative z-potential and a good stability, at least up to one month. Integrity studies performed in the presence of serum proteins indicated that these decorated nanoliposomes fulfill the requirements for in vivo applications. NMR experiments carried out with A beta-(1-42) oligomers using both surface functionalized and plain (control) liposomes, revealed that the binding ability of the nanoliposomes was mediated by the presence of the tricyclic ligand on their surface. Finally ThT assay carried out with tricyclic-decorated liposomes showed significant decrease in thioflavine T fluorescence after 24 h, suggesting a significant inhibition/delay of A beta(1-42) aggregation. (C) 2014 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2014.07.085
• 作为产物：
  描述：

  (2R,3R,4R,4aR,5R,10aR)-3,4-bis(benzyloxy)-2-benzyloxymethyl-5-methoxy-7-methyl-2,3,4,4a,5,10a-hexahydropyrano[2,3-b]chromene 在 氢气 、 palladium(II) hydroxide 作用下， 以 甲醇 、 乙酸乙酯 为溶剂， 以95%的产率得到(2R,3R,4R,4aS,5R,10aR)-2-hydroxymethyl-5-methoxy-7-methyl-2,3,4,4a,5,10a-hexahydropyrano[2,3-b]chromen-3,4-diol
  参考文献：
  名称：

  cis-Glyco-fused benzopyran compounds as new amyloid-β peptide ligands

  摘要：

  我们合成了一个小型的糖融合苯并吡喃化合物库。通过 STD-NMR 和 trNOESY 实验分析了它们与 Aδ肽的相互作用特征。此外，还通过分子力学（MM）和分子动力学（MD）模拟对这些化合物进行了构象分析。

  DOI：

  10.1039/c1cc13046c

文献信息

• [EN] NEW TRICYCLIC COMPOUNDS, PROCESS FOR THEIR MANUFACTURE AND THEIR USE AS LIGANDS OF THE BETA AMYLOID PEPTIDES<br/>[FR] NOUVEAUX COMPOSÉS TRICYCLIQUES, LEUR PROCÉDÉ DE FABRICATION ET LEUR UTILISATION EN TANT QUE LIGANDS DES PEPTIDES BÊTA-AMYLOÏDES
  申请人：UNI DEGLI STUDIO DI MILANO BICOCCA

  公开号：WO2012164476A1

  公开（公告）日：2012-12-06

  The synthesis and the use of the compounds with glycofused tricyclic structure as ligands of the Αβ peptides is the object of the invention. Such compounds result to be chemically stable, they have a high solubility under physiological conditions and they are suitable for functionalizations which make them easily conjugable to other entities to allow a therapeutic and diagnostic use thereof. The capability of the compounds to link the Αβ peptide, in the various shapes thereof, and in particular the most toxic one, represented by the oligomers, was evaluated through NMR experiments.(III).

  本发明的目标是合成和使用具有糖基融合三环结构的化合物作为Αβ肽配体。这些化合物具有化学稳定性，在生理条件下具有高溶解度，并且适合进行功能化，使它们易于与其他实体结合，以允许其进行治疗和诊断使用。通过NMR实验评估了这些化合物与Αβ肽的连接能力，特别是与寡聚体形式的最有毒的形式。