5,7-Bis-benzyloxy-2-(3,4,5-tris-benzyloxy-phenyl)-chroman-3-ol | 896121-45-2

• 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: 5,7-Bis-benzyloxy-2-(3,4,5-tris-benzyloxy-phenyl)-chroman-3-ol
• 英文别名: (2R,3S)-5,7-bis(benzyloxy)-2-(3,4,5-tris(benzyloxy)phenyl)chroman-3-ol；5,7-bis(phenylmethoxy)-2-[3,4,5-tris(phenylmethoxy)phenyl]-3,4-dihydro-2H-chromen-3-ol
• CAS: 896121-45-2
• 化学式: C₅₀H₄₄O₇
• 分子量: 756.895
• InChiKey: GKTZINGANAELDT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.2
• 重原子数：
  57
• 可旋转键数：
  16
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  75.6
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  5,7-Bis-benzyloxy-2-(3,4,5-tris-benzyloxy-phenyl)-chroman-3-ol 在 palladium on activated charcoal N-甲基吗啉 、 4-二甲氨基吡啶 、 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 (-)-没食子儿茶素-3-没食子酸酯
  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：

  3,4,5-三(苯甲氧基)苯甲醛 在 sodium tetrahydroborate 、 硼烷四氢呋喃络合物 、 sodium hydride 作用下， 以 四氢呋喃 、 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 生成 5,7-Bis-benzyloxy-2-(3,4,5-tris-benzyloxy-phenyl)-chroman-3-ol
  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

文献信息

• Analogs of green tea polyphenols as chemotherapeutic and chemopreventive agents
  申请人：——

  公开号：US20040110790A1

  公开（公告）日：2004-06-10

  Novel compounds useful as chemotherapeutic and chemopreventive agents are provided. The compounds are analogs of polyphenol catechins that occur in green tea, such as epigallocatichin-3-gallate (EGCG), and have the structure of formula (I) 1 wherein R 1 through R 11 are defined herein. Preferred R 4 moieties are selected from O, S, NH and CH 2 , and in exemplary compounds, R 4 is O and R 5 is a tri-substituted aroyloxy substituent, such as a 3,4,5-substituted benzoyloxy group. Pharmaceutical compositions are provided as well, as are methods of chemotherapy and chemoprevention.

  提供了作为化疗和化学预防剂有用的新型化合物。这些化合物是绿茶中存在的多酚儿茶素的类似物，如表儿茶素-3-没食子酸酯（EGCG），其结构如式（I）1所示，其中R1至R11在此处定义。首选的R4基团从O、S、NH和CH2中选择，在示例化合物中，R4为O，R5为三取代芳酰氧基取代基，如3,4,5-取代苯甲酰氧基基团。还提供了药物组合物，以及化疗和化学预防的方法。
• Real‐Time Analysis of Polyphenol–Protein Interactions by Surface Plasmon Resonance Using Surface‐Bound Polyphenols
  作者：Daniela Mélanie Delannoy López、Dong Tien Tran、Guillaume Viault、Sofiane Dairi、Philippe Alexandre Peixoto、Yoan Capello、Laëtitia Minder、Laurent Pouységu、Elisabeth Génot、Carmelo Di Primo、Denis Deffieux、Stéphane Quideau

  DOI：10.1002/chem.202005187

  日期：2021.3.22

  evaluate in real time by surface plasmon resonance (SPR) the interactions of three different surface‐bound polyphenolic ligands per sensor chip with various protein analytes, including human DNA topoisomerase IIα, flavonoid leucoanthocyanidin dioxygenase, B‐cell lymphoma 2 apoptosis regulator protein, and bovine serum albumin. The types and levels of SPR responses unveiled major differences in the association

  对不同结构类别的生物活性多酚进行了化学修饰，使其具有不同的生物结构，如鞣花单宁，维斯卡林和黄花青素，黄酮儿茶素，表儿茶素，表没食子儿茶素没食子酸酯（EGCG）和原花青素B2。使它们固定在链霉亲和素包被的传感器芯片上。这些传感器芯片用于通过表面等离子体共振（SPR）实时评估每个传感器芯片上三种不同的表面结合多酚配体与各种蛋白质分析物之间的相互作用，包括人类DNA拓扑异构酶IIα，类黄酮类花色素二加氧合酶，B细胞淋巴瘤2凋亡调节蛋白和牛血清白蛋白。SPR回应的类型和水平揭示了这种关联中的主要差异，或者缺乏关联，在给定的蛋白质分析物和不同的多酚配体之间发生解离。因此，这种多分析SPR技术是快速筛选和定性比较各种多酚-蛋白质相互作用的有价值的方法。
• Polyphenol proteasome inhibitors, synthesis, and methods of use
  申请人：——

  公开号：US20040186167A1

  公开（公告）日：2004-09-23

  The present invention relates to synthetic green tea derived polyphenolic compounds, their modes of syntheses, and their use in inhibiting proteasomal activity and in treating cancers. The present invention is also directed to pharmaceutical compositions useful in methods of inhibiting proteasomes and of treating cancers.

  本发明涉及合成的绿茶多酚化合物，它们的合成方式以及它们在抑制蛋白酶体活性和治疗癌症方面的应用。本发明还涉及用于抑制蛋白酶体和治疗癌症的药物组合物。
• Polyphenol Proteasome Inhibitors, Synthesis, and Methods of Use
  申请人：DOU Q. Ping

  公开号：US20120029067A1

  公开（公告）日：2012-02-02

  The present invention relates to synthetic green tea derived polyphenolic compounds, their modes of syntheses, and their use in inhibiting proteasomal activity and in treating cancers. The present invention is also directed to pharmaceutical compositions useful in methods of inhibiting proteasomes and of treating cancers.

  本发明涉及合成的绿茶多酚类化合物，它们的合成方式以及它们在抑制蛋白酶体活性和治疗癌症方面的应用。本发明还涉及制药组合物，用于抑制蛋白酶体和治疗癌症的方法。
• POLYPHENOL PROTEASOME INHIBITORS, SYNTHESIS, AND METHODS OF USE
  申请人：UNIVERSITY OF SOUTH FLORIDA

  公开号：US20140045931A1

  公开（公告）日：2014-02-13

  The present invention relates to synthetic green tea derived polyphenolic compounds, their modes of syntheses, and their use in inhibiting proteasomal activity and in treating cancers. The present invention is also directed to pharmaceutical compositions useful in methods of inhibiting proteasomes and of treating cancers.

  本发明涉及合成绿茶多酚化合物及其合成方式，以及它们在抑制蛋白酶体活性和治疗癌症方面的应用。本发明还涉及制备药物组合物，用于抑制蛋白酶体和治疗癌症的方法。