5,7-dibenzyloxy-2-[3,4,5-tris(benzyloxy)phenyl]-2H-chromene | 333796-78-4

• 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-dibenzyloxy-2-[3,4,5-tris(benzyloxy)phenyl]-2H-chromene
• 英文别名: 5,7,3',4',5'-pentabenzyloxyflav-3-ene；5,7-bis(phenylmethoxy)-2-[3,4,5-tris(phenylmethoxy)phenyl]-2H-chromene
• CAS: 333796-78-4
• 化学式: C₅₀H₄₂O₆
• 分子量: 738.88
• InChiKey: ANPRRTRFKZTGEC-UHFFFAOYSA-N

物化性质

• 熔点：
  105-107 °C
• 沸点：
  860.8±65.0 °C(Predicted)
• 密度：
  1.214±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  11.3
• 重原子数：
  56
• 可旋转键数：
  16
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  55.4
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  5,7-dibenzyloxy-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 (-)-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：

  没食子酸甲酯 在 哌啶 、 sodium tetrahydroborate 、 lithium aluminium tetrahydride 、 potassium carbonate 、 pyridinium chlorochromate 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 5,7-dibenzyloxy-2-[3,4,5-tris(benzyloxy)phenyl]-2H-chromene
  参考文献：
  名称：

  Synthesis of a 3,4,5-Trimethoxybenzoyl Ester Analogue of Epigallocatechin-3-gallate (EGCG):  A Potential Route to the Natural Product Green Tea Catechin, EGCG

  摘要：

  [GRAPHICS]The synthesis of a trimethoxybenzoyl ester (D-ring) analogue of epigallocatechin-3-gallate (EGCG) is described. The versatile synthesis route can be used to synthesize A, B, and D ring analogues of EGCG and involves a key cyclization of the chalcone to the 3-flavene. This synthesis provides a possible route to the polyphenolic green tea natural product EGCG.

  DOI：

  10.1021/ol007000o

文献信息

• Enantioselective Synthesis of Flavan-3-ols Using a Mitsunobu Cyclization
  作者：Karsten Krohn、Ishtiaq Ahmed、Markus John

  DOI：10.1055/s-0028-1083361

  日期：——

  The synthesis of four flavan-3-ols with different substitution patterns and electron densities has been achieved in high stereo- and regioselectivity by a one-step Mitsunobu reaction from the corresponding diols, which were prepared by enantioselective Sharpless dihydroxylation of suitable olefins. The six-membered flavan-3-ols were the only cyclization products and the theoretically possible formation of five-membered rings during the Mitsunobu cyclization was not observed. The flavanols are important starting materials for the synthesis of dimers such as the procyanidins or other coupling products such as the flavan part of the potent DNA polymerase β inhibitor myristinin A. The enantioselectivities of both the Sharpless dihydroxylation and the Mitsunobu cyclization steps were monitored by chiral HPLC.

  通过从相应的二醇进行一步Mitsunobu反应，以高立体选择性和区位选择性成功合成了四种具有不同取代模式和电子密度的黄酮-3-醇，这些二醇是通过对合适的烯烃进行手性选择性的Sharpless二羟基化制备的。在Mitsunobu环化过程中，六元环的黄酮-3-醇是唯一的环化产物，理论上可能形成的五元环并未被观察到。这些黄酮醇是合成二聚体（如原花青素）或其他偶联产物（如强效DNA聚合酶β抑制剂myristinin A中的黄酮部分）的重要起始材料。Sharpless二羟基化和Mitsunobu环化步骤的对映选择性通过手性高效液相色谱法进行了监测。
• METHOD FOR PRODUCING FLAVAN DERIVATIVE
  申请人：Suzuki Keisuke

  公开号：US20090099374A1

  公开（公告）日：2009-04-16

  The present invention provides a method for producing flavan derivatives having various substituent groups with controlling the stereochemistry. The method of the present invention includes the steps of: hydratively condensing a phenol compound expressed by formula (I) and an alcohol compound expressed by formula (II) to from an epoxide compound of formula (III); opening the epoxy ring of the epoxide compound of formula (III) to form an iodine-containing compound of formula (IV); and cyclizing the iodine-containing compound to form the flavan derivative of formula (V).
• US7820835B2
  申请人：——

  公开号：US7820835B2

  公开（公告）日：2010-10-26
• A structure-activity study for the inhibition of metalloproteinase-9 activity and gene expression by analogues of gallocatechin-3-gallate
  作者：M. Dell’Agli、S. Bellosta、L. Rizzi、G. V. Galli、M. Canavesi、F. Rota、R. Parente、E. Bosisio、S. Romeo

  DOI：10.1007/s00018-005-5422-7

  日期：2005.12

  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.
• Synthesis of a 3,4,5-Trimethoxybenzoyl Ester Analogue of Epigallocatechin-3-gallate (EGCG):  A Potential Route to the Natural Product Green Tea Catechin, EGCG
  作者：Nurulain T. Zaveri

  DOI：10.1021/ol007000o

  日期：2001.3.1

  [GRAPHICS]The synthesis of a trimethoxybenzoyl ester (D-ring) analogue of epigallocatechin-3-gallate (EGCG) is described. The versatile synthesis route can be used to synthesize A, B, and D ring analogues of EGCG and involves a key cyclization of the chalcone to the 3-flavene. This synthesis provides a possible route to the polyphenolic green tea natural product EGCG.