2-(3,4,5-tris(benzyloxy)phenyl)-2H-chromene | 896121-43-0

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 黄酮类化合物
• 英文名称: 2-(3,4,5-tris(benzyloxy)phenyl)-2H-chromene
• 英文别名: 2-[3,4,5-tris(phenylmethoxy)phenyl]-2H-chromene
• CAS: 896121-43-0
• 化学式: C₃₆H₃₀O₄
• 分子量: 526.632
• InChiKey: XOUBAFCEOSKWRZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.57
• 重原子数：
  40.0
• 可旋转键数：
  10.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  36.92
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  2-(3,4,5-tris(benzyloxy)phenyl)-2H-chromene 在 palladium on activated charcoal N-甲基吗啉 、 4-二甲氨基吡啶 、 硼烷四氢呋喃络合物 、 氢气 、 O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate 作用下， 以 四氢呋喃 、 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 生成 (+/-)-trans-3,3',4',5'-flavantetrol 3-O-gallate
  参考文献：
  名称：

  A structure-activity study for the inhibition of metalloproteinase-9 activity and gene expression by analogues of gallocatechin-3-gallate

  摘要：

  Catechins are able to modulate the gelatinolytic activity of matrix metalloproteinase-9 (MMP-9) by reducing its release from macrophages. Gallocatechins decrease MMP-9 secretion by lowering MMP-9 promoter activity and mRNA levels. The effect appears to be dependent on some structural and stereochemical requirements. In this study, the relationship between chemical structure and activity was studied by testing the effect of analogues of (+/-)-gallocatechin-3-gallate (+/-)-GCG, selectively deprived of hydroxyl groups, on MMP-9 activity, transcription, and secretion. Our results indicate that (+/-)-GCG and (+/-)-catechin-3-gallate are characterized by a substitution pattern compatible with direct inhibition of MMP-9 activity. Conversely, when transcription was the target, (+/-)-trans-3-flavanol-3-benzoate, lacking all the hydroxyl groups, was the most effective both in lowering MMP-9 promoter activity and consequently protein secretion, and in inhibiting nuclear-factor-kappa B-driven transcription. Our results suggest that the structural requirements for enzyme inhibition are different from those necessary for targeting gene expression.

  DOI：

  10.1007/s00018-005-5422-7
• 作为产物：
  描述：

  没食子酸 在 sodium tetrahydroborate 、 lithium aluminium tetrahydride 、 cerium(III) chloride 、 硫酸 、 potassium carbonate 、 pyridinium chlorochromate 、 potassium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 76.0h， 生成 2-(3,4,5-tris(benzyloxy)phenyl)-2H-chromene
  参考文献：
  名称：

  [EN] COMPOSITIONS AND METHODS FOR ANTIOXIDANT AND ANTI-INFLAMMATORY THERAPEUTICS
  [FR] COMPOSITIONS ET PROCÉDÉS POUR DES AGENTS THÉRAPEUTIQUES ANTIOXYDANTS ET ANTI-INFLAMMATOIRES

  摘要：

  The present invention relates to compositions and methods for antioxidant and anti-inflammatory therapeutics.

  公开号：

  WO2023288020A1

文献信息

• Design, synthesis, and biological evaluation of polyphenol derivatives as DYRK1A inhibitors. The discovery of a potentially promising treatment for Multiple Sclerosis
  作者：Gian Luca Araldi、Yu-Wen Hwang

  DOI：10.1016/j.bmcl.2022.128675

  日期：2022.5