4'-O-methylepigallocatechin-3-O-gallate

• 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: 4'-O-methylepigallocatechin-3-O-gallate
• 英文别名: (-)-(2R,3R)-5,7-dihydroxy-2-(3',5'-bis(benzyloxy)-4'-methoxyphenyl)chroman-3-yl 3'',4'',5''-trihydroxybenzoate；(2R,3R)-2-(3,5-dihydroxy-4-methoxyphenyl)-5,7-dihydroxychroman-3-yl 3,4,5-trihydroxybenzoate；(-)-4'-O-methylepigallocatechin-3-O-gallate；4'-O-methyl-(-)-epigallocatechin-3-gallate；(-)-4'-O-methylepigallocatechin 3-gallate；4'-O-methyl-(-)-epigallocatechin gallate；[(2R,3R)-2-(3,5-dihydroxy-4-methoxyphenyl)-5,7-dihydroxy-3,4-dihydro-2H-chromen-3-yl] 3,4,5-trihydroxybenzoate
• 化学式: C₂₃H₂₀O₁₁
• 分子量: 472.405
• InChiKey: NPUWDJQZPQKPAA-TZIWHRDSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  34
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  186
• 氢给体数：
  7
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  4'-O-methylepigallocatechin-3-O-gallate 、 3,5-二甲氧基-4-苯甲氧基安息香酸盐 在 4-二甲氨基吡啶 、 N,N'-二异丙基碳二亚胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 36.0h， 生成 7-fluoro-3-methyl-quinoline
  参考文献：
  名称：

  组合甲基化（±）-表没食子儿茶素没食子酸酯库的固相合成及其对黑素瘤B16细胞的生长抑制作用

  摘要：

  我们报告了组合甲基化（±）-表没食子儿茶素没食子酸酯（EGCG）库的固相合成及其生物学评估。儿茶素家族的成员表没食子儿茶素没食子酸酯（EGCG）及其甲基化衍生物具有多种抗癌作用。甲基化EGCG的固相合成涉及通过固相负载的醛与酮和酸的偶联来制备α-酰氧基酮。固体负载的α-酰氧基酮的后续释放和还原醚化反应以良好的总收率提供了受保护的EGCG。成功制备了64种甲基化EGCG。还检查了甲基化EGCG文库的生长抑制作用。尽管EGCG的甲基化通常会导致生长抑制作用降低，7-OMe EGCG的生长抑制作用与EGCG相当。7-OMe EGCG由于具有更高的生物利用度，因此是有吸引力的候选药物。

  DOI：

  10.1002/asia.201000372
• 作为产物：
  描述：

  3,4,5-三苄氧基苯甲酸 在 palladium dihydroxide 4-二甲氨基吡啶 、 草酰氯 、 氢气 、 N,N-二甲基甲酰胺 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 9.0h， 生成 4'-O-methylepigallocatechin-3-O-gallate
  参考文献：
  名称：

  Regiospecific and enantioselective synthesis of methylated metabolites of tea catechins

  摘要：

  The regiospecific and enantioselective syntheses of various methylated regioisomers of epicatechin gallate (EGC) and epigallocatechin gallate (EGCG) have been achieved. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.04.010

文献信息

• Syntheses of methylated catechins and theaflavins using 2-nitrobenzenesulfonyl group to protect and deactivate phenol
  作者：Tomohiro Asakawa、Yusuke Kawabe、Atsushi Yoshida、Yoshiyuki Aihara、Tamiko Manabe、Yoshitsugu Hirose、Asuka Sakurada、Makoto Inai、Yoshitaka Hamashima、Takumi Furuta、Toshiyuki Wakimoto、Toshiyuki Kan

  DOI：10.1038/ja.2016.14

  日期：2016.4

  An efficient and versatile synthetic method for labile polyphenols was established using 2-nitrobenzenesulfonate (Ns) as a protecting group for phenol. This methodology provides regio- and stereoselective access to a range of methylated catechins, such as methylated epigallocatechin gallates, that are not readily available from natural sources. In addition, biomimetic synthesis of theaflavins from

  使用2-硝基苯磺酸盐（Ns）作为酚的保护基，建立了一种有效且通用的不稳定多酚合成方法。这种方法为区域和立体选择提供了一系列甲基化的儿茶素，例如甲基化的表没食子儿茶素没食子酸酯，而天然来源不易获得。此外，使用Ns保护可从儿茶素仿生合成茶黄素，从而最大程度地减少了氧化过程中富电子芳环的不良副反应，从而能够在一步氧化偶联反应中构建复杂的苯并马酚酮核。这些化合物的可用性将有助于儿茶素的详细结构生物学活性关系研究。
• METHODS OF TREATING COGNITIVE AND BEHAVIORAL IMPAIRMENT IN DOWN SYNDROME AND ALZHEIMERS DISEASE PATIENTS
  申请人：AVANTI BIOSCIENCES, INC.

  公开号：US20180000774A1

  公开（公告）日：2018-01-04

  The present invention relates to methods of treating cognitive and behavioral impairment in Down syndrome and/or Alzheimer's disease patients, Alzheimer's disease, neurodegenerative disease, cancer, DYRK1A-mediated disorders and methods of modulating and inhibiting DYRK1-A comprising use of catechins.

  本发明涉及治疗唐氏综合症和/或阿尔茨海默病患者认知和行为障碍的方法，阿尔茨海默病，神经退行性疾病，癌症，DYRK1A介导的疾病以及使用儿茶素调节和抑制DYRK1-A的方法。
• Regioselective synthesis of methylated epigallocatechin gallate via nitrobenzenesulfonyl (Ns) protecting group
  作者：Yoshiyuki Aihara、Atsusi Yoshida、Takumi Furuta、Toshiyuki Wakimoto、Toshifumi Akizawa、Motomi Konishi、Toshiyuki Kan

  DOI：10.1016/j.bmcl.2009.05.111

  日期：2009.8

  Regioselective synthesis of methylated epigallocatechin gallate from epigallocatechin was accomplished using a 2-nitrobenzenesulfonyl (Ns) group as a protecting group for phenols. This methodology provided several methylated catechins, which are naturally scarce catechin derivatives. (C) 2009 Elsevier Ltd. All rights reserved.
• Relationship between the Biological Activities of Methylated Derivatives of (−)-Epigallocatechin-3-<i>O</i>-gallate (EGCG) and Their Cell Surface Binding Activities
  作者：Satomi Yano、Yoshinori Fujimura、Daisuke Umeda、Toshio Miyase、Koji Yamada、Hirofumi Tachibana

  DOI：10.1021/jf071176o

  日期：2007.8.1

  It was previously reported that (-)-epigallocatechin-3-O-gallate (EGCG) suppresses the expression of the high-affinity IgE receptor Fc epsilon RI in human basophilic cells and that this suppressive effect is associated with EGCG binding to the cell surface. This study examined the effects of five methylated derivatives of EGCG, (-)-epigallocatechin-3-O-(3-O-methyl)gallate (EGCG 3 '' Me), (-)-epigallocatechin-3-O-(4-O-methyl)gallate (EGCG 4 '' Me), (-)-4'-O-methyl-epigallocatechin-3-O-gallate (EGCG 4'Me), (-)-epigallocatechin-3-O-(3,4-O-methyl)gallate (EGCG 3 '' 4 '' diMe), and (-)-4'-O-methyl-epigallocatechin-3-O-(4-O-methyl)gallate (EGCG 4'4 '' diMe) on Fc epsilon RI expression and ERK1/2 phosphorylation, and each of their cell surface binding activities was measured. Of these five methylated derivatives, three that are methylated at the 3 ''- and/or 4 ''-position, EGCG 3 '' Me, EGCG 4 '' Me, and EGCG 3 '' 4 '' diMe, suppressed Fc epsilon RI expression and ERK1/2 phosphorylation, although the suppressive effects were lower than that of EGCG. EGCG 4'Me and EGCG 4'4 '' diMe, both of which are methylated at the 4'-position, did not demonstrate a suppressive effect. Furthermore, it was found that EGCG 3 '' Me, EGCG 4 '' Me, EGCG 3 '' 4 '' diMe, and EGCG 4'Me, which are methylated at the 3 ''- and/or 4 ''-positions or the 4'-position, could bind to the cell surface even though their binding activities were lower than that of EGCG. Only EGCG 4'4 '' diMe, which is methylated at both the 4'- and 4 ''-positions, could not bind. These results suggest that the trihydroxyl structure of the B ring is essential for EGCG to exert the suppressive effects and that the hydroxyl groups on both the 4'-position in the B ring and the 4 ''-position in the gallate are crucial for the cell surface binding activity of EGCG.
• CONJUGATES OF HUPERZINE AND ANALOGS THEREOF
  申请人：INSERO HEALTH INC.

  公开号：US20150191430A1

  公开（公告）日：2015-07-09

  Compounds and compositions for treating neurodegenerative diseases are described. The compounds include a therapeutic agent covalently linked with huperzine or an analog thereof through a linker. Methods of preparing the compounds are described. Methods of treating a neurodegenerative disease by administering compounds and compositions including a therapeutic agent covalently linked with huperzine or an analog thereof are described. Methods for delivering a therapeutic agent by administering the therapeutic agent covalently linked to huperzine or an analog thereof are described.