(-)-没食子儿茶素-3-没食子酸酯 | 5127-64-0

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 黄酮类化合物
• 中文名称: (-)-没食子儿茶素-3-没食子酸酯
• 中文别名: 没食子儿茶素没食子酸酯
• 英文名称: (+)-gallocatechin 3-O-gallate
• 英文别名: (+)-GCG；(2R,3S)-5,7-dihydroxy-2-(3,4,5-trihydroxyphenyl)chroman-3-yl 3,4,5-trihydroxybenzoate；(−)-epigallocatechin gallate；(+)-Gallocatechin-3-O-gallate；(-)-gallocatechin 3-O-gallate；(+)-gallocatechin 3-gallate；Gallocatechin gallate；[(2R,3S)-5,7-dihydroxy-2-(3,4,5-trihydroxyphenyl)-3,4-dihydro-2H-chromen-3-yl] 3,4,5-trihydroxybenzoate
• CAS: 5127-64-0
• 化学式: C₂₂H₁₈O₁₁
• 分子量: 458.378
• InChiKey: WMBWREPUVVBILR-GHTZIAJQSA-N

物化性质

• 熔点：
  248-249 °C
• 沸点：
  909.1±65.0 °C(Predicted)
• 密度：
  1.90±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  33
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  197
• 氢给体数：
  8
• 氢受体数：
  11

安全信息

• 储存条件：
  保存在2-8℃的环境中，需要干燥并密封。

反应信息

• 作为反应物：
  描述：

  (-)-没食子儿茶素-3-没食子酸酯 生成 [(2R,3S)-5,7-diacetyloxy-2-(3,4,5-triacetyloxyphenyl)-3,4-dihydro-2H-chromen-3-yl] 3,4,5-triacetyloxybenzoate
  参考文献：
  名称：

  PETEREIT, FRANK;KOLODZIEJ, HERBERT;NAHRSTEDT, ADOLF, PHYTOCHEMISTRY, 30,(1991) N, C. 981-985

  摘要：

  DOI：
• 作为产物：
  描述：

  [(2R,3S)-5,7-bis(phenylmethoxy)-2-[3,4,5-tris(phenylmethoxy)phenyl]-3,4-dihydro-2H-chromen-3-yl] 3,4,5-tris(phenylmethoxy)benzoate 在 palladium(II) hydroxide/carbon 氢气 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 4.0h， 以74%的产率得到(-)-没食子儿茶素-3-没食子酸酯
  参考文献：
  名称：

  Polyphenol proteasome inhibitors, synthesis, and methods of use

  摘要：

  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。

  公开号：

  US20040186167A1

文献信息

• Flavan-3-ols and proanthocyanidins from Cistus incanus
  作者：Frank Petereit、Herbert Kolodziej、Adolf Nahrstedt

  DOI：10.1016/0031-9422(91)85291-7

  日期：1991.1

  seven oligomeric flavanoids have been identified from a Cistus incanus subspecies traditionally used for treatment of skin diseases in northern parts of Greece and identified as subsp. tauricus. Flavan-3-ols are (+)-catechin, (+)-gallocatechin, the novel (+)-gallocatechin 3-gallate and the rarely occurring (+)-catechin 3-O-α-β-rhamnoside; proanthocyanidins are procyanidins B1 and B3, gallocatechin-(4α

  摘要 已从传统上用于治疗希腊北部皮肤病的岩蔷薇亚种中鉴定出四种单体和七种寡聚类黄酮，并被鉴定为亚种。金牛座。Flavan-3-ols 是 (+)-catechin, (+)-gallocatechin, new (+)-gallocatechin 3-gallate 和罕见的 (+)-catechin 3-O-α-β-rhamnoside; 原花青素是原花青素 B1 和 B3，没食子儿茶素-(4α → 8)-没食子儿茶素，其新型 (4α → 6)-区域异构体，没食子儿茶素-(4α → 8)-儿茶素，初步鉴定的新型儿茶素-(4α → 8)-没食子儿茶素和三聚体没食子儿茶素-(4α → 8)-没食子儿茶素-(4α → 8)-儿茶素。还获得了罕见的黄烷酮2R,3R-二氢杨梅素。
• Reagent-controlled stereoselective synthesis of (±)-gallo- and (±)-epigallo-catechin gallates
  作者：Hiroshi Tanaka、Ayaka Chino、Takashi Takahashi

  DOI：10.1016/j.tetlet.2012.02.065

  日期：2012.5

  Synthesis of (±)-gallocatechin and (±)-epigallocatechin gallates by electrophilic cycloarylation is reported. The precursors for cyclization were prepared by reagent-controlled stereo-selective opening of epoxide with phenol. Activation of the S-oxidized S,O-acetal enabled electrophilic cycloarylation to stereoselectively provide the acylated catechins.

  报道了通过亲电环芳基化反应合成（±）-没食子儿茶素和（±）-表没食子儿茶素没食子酸酯。用于环化的前体是通过试剂控制的酚与酚的立体选择性开环而制得的。在激活小号-oxidized小号，Ø -acetal启用电子cycloarylation立体选择性地提供酰化的儿茶素。
• 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。
• NMR spectroscopic characterization of inclusion complexes comprising cyclodextrins and gallated catechins in aqueous solution: cavity size dependency
  作者：Takashi Ishizu、Hiroyuki Tsutsumi、Hideji Yamamoto、Kazunobu Harano

  DOI：10.1002/mrc.2383

  日期：2009.4

  In the 1:1 inclusion complex with GCg and gamma-CD, the GCg moiety maintained a conformation in which the B and B' rings of GCg took both pseudoequatorial positions with respect to the C ring. The structure of the inclusion complex of GCg and gamma-CD obtained from NMR experiments supported well that determined from PM6 semiempirical SCF MO calculations. However, (1)H NMR experiments suggested that EGCg

  使用几种NMR技术研究了D（2）O中γ-环糊精（γ-CD），（-）-没食子儿茶素没食子酸酯（GCg）和（-）-表没食子儿茶素没食子酸酯（EGCg）包合物的结构。GCg与γ-CD形成了1：1的包合物，其中GCg的A和C环从宽的仲羟基一侧深处插入A环的头部，进入γ-CD腔。在具有GCg和γ-CD的1∶1包合物中，GCg部分保持这样的构型，其中GCg的B和B′环相对于C环占据两个伪赤道位置。由NMR实验获得的GCg和γ-CD包合物的结构很好地支持了PM6半经验SCF MO计算所确定的结果。然而，（1）H NMR实验表明，EGCg在D（2）O中未与γ-CD形成任何包合物。可以通过用PM6方法计算出的稳定能来解释GCg和EGCg在对γ-CD的夹杂行为方面的显着差异。。
• CHEMICAL COMPOUNDS
  申请人：Axten Jeffrey Michael

  公开号：US20120077828A1

  公开（公告）日：2012-03-29

  The invention is directed to substituted indoline derivatives. Specifically, the invention is directed to compounds according to Formula I: wherein R 1 , R 2 , and R 3 are defined herein. The compounds of the invention are inhibitors of PERK and can be useful in the treatment of cancer, ocular diseases, and diseases associated with activated unfolded protein response pathways, such as Alzheimer's disease, stroke, Type 1 diabetes Parkinson disease, Huntington's disease, amyotrophic lateral sclerosis, myocardial infarction, cardiovascular disease, atherosclerosis, and arrhythmias, and more specifically cancers of the breast, colon, pancreatic, and lung. Accordingly, the invention is further directed to pharmaceutical compositions comprising a compound of the invention. The invention is still further directed to methods of inhibiting PERK activity and treatment of disorders associated therewith using a compound of the invention or a pharmaceutical composition comprising a compound of the invention.

  本发明涉及取代的吲哚啉衍生物。具体而言，本发明涉及按式I所示的化合物：其中R1、R2和R3在此定义。本发明的化合物是PERK的抑制剂，可用于治疗癌症、眼部疾病和与激活的未折叠蛋白质应答途径相关的疾病，如阿尔茨海默病、中风、1型糖尿病帕金森病、亨廷顿病、肌萎缩性侧索硬化、心肌梗死、心血管疾病、动脉硬化和心律失常，更具体地，乳腺癌、结肠癌、胰腺癌和肺癌。因此，本发明进一步涉及包含本发明化合物的药物组合物。本发明还涉及使用本发明化合物或包含本发明化合物的药物组合物抑制PERK活性和治疗相关疾病的方法。