2-(2,2-diphenylbenzo[1,3]dioxol-5-yl)-3-(2,3,4,6-tetra-O-acetyl)-β-D-glucopyranosyloxy-5,7-dihydroxy-4H-chromen-4-one | 477244-18-1

• 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-(2,2-diphenylbenzo[1,3]dioxol-5-yl)-3-(2,3,4,6-tetra-O-acetyl)-β-D-glucopyranosyloxy-5,7-dihydroxy-4H-chromen-4-one
• 英文别名: 2-(2,2-diphenylbenzo[d][1,3]dioxol-5-yl)-5,7-dihydroxy-3-β-D-tetraacetylglucosyl-4H-chromen-4-one；2-(2,2-diphenyl-benzo[1,3]dioxolan-5-yl)-3-O-β-D-tetraacetylglucopyranosyl-5,7-dihydroxy-benzopyran-4-one；[(2R,3R,4S,5R,6S)-3,4,5-triacetyloxy-6-[2-(2,2-diphenyl-1,3-benzodioxol-5-yl)-5,7-dihydroxy-4-oxochromen-3-yl]oxyoxan-2-yl]methyl acetate
• CAS: 477244-18-1
• 化学式: C₄₂H₃₆O₁₆
• 分子量: 796.738
• InChiKey: QWCBPQKOWJRJMB-NNGHHDDZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  58
• 可旋转键数：
  14
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  209
• 氢给体数：
  2
• 氢受体数：
  16

反应信息

• 作为反应物：
  描述：

  2-(2,2-diphenylbenzo[1,3]dioxol-5-yl)-3-(2,3,4,6-tetra-O-acetyl)-β-D-glucopyranosyloxy-5,7-dihydroxy-4H-chromen-4-one 在 sodium hypochlorite 、 2,2,6,6-四甲基哌啶氧化物 、 四丁基溴化铵 、 sodium methylate 、 potassium carbonate 、 potassium bromide 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 17.5h， 生成
  参考文献：
  名称：

  Regiospecific synthesis of quercetin O-β-d-glucosylated and O-β-d-glucuronidated isomers

  摘要：

  Quercetin, the polyphenolic compound, which has the highest daily intake, is well known for its protective effects against aging diseases and has received a lot of attention for this reason. Both quercetin 3-O-beta-D-glucuronide and quercetin 3'-O-beta-D-glucuronide are human metabolites, which, together with their regioisomers, are required for biological as well as physical chemistry studies. We present here a novel synthetic route based on the sequential and selective protections of the hydroxyl functions of quercetin allowing selective glycosylation, followed by TEMPO-mediated oxidation to the glucuronide. This methodology enabled us to synthesize the five O-beta-D-glucosides and four O-beta-D-glucuronides of quercetin, including the major human metabolite, quercetin 3-O-beta-D-glucuronide. (C) 2011 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tet.2011.03.110
• 作为产物：
  描述：

  β-D-葡萄糖五乙酸酯 在 氢溴酸 、 potassium carbonate 、 溶剂黄146 作用下， 以 丙酮 为溶剂， 反应 14.0h， 生成 2-(2,2-diphenylbenzo[1,3]dioxol-5-yl)-3-(2,3,4,6-tetra-O-acetyl)-β-D-glucopyranosyloxy-5,7-dihydroxy-4H-chromen-4-one
  参考文献：
  名称：

  NOVEL FLAVANONE DERIVATIVE

  摘要：

  公开号：

  EP2460810B1

文献信息

• Binding interaction of quercetin-3-β-galactoside and its synthetic derivatives with SARS-CoV 3CLpro: Structure–activity relationship studies reveal salient pharmacophore features
  作者：Lili Chen、Jian Li、Cheng Luo、Hong Liu、Weijun Xu、Gang Chen、Oi Wah Liew、Weiliang Zhu、Chum Mok Puah、Xu Shen、Hualiang Jiang

  DOI：10.1016/j.bmc.2006.09.014

  日期：2006.12

  enzymatic activity of SARS-CoV 3CL(pro) were not affected by the Q189A mutation. With the help of molecular modeling, eight new derivatives of the natural product were designed and synthesized. Bioassay results reveal salient features of the structure-activity relationship of the new compounds: (1) removal of the 7-hydroxy group of the quercetin moiety decreases the bioactivity of the derivatives; (2)

  严重急性呼吸综合征相关冠状病毒 (SARS-CoV) 的 3C 样蛋白酶 (3CL(pro)) 是发现抗 SARS 药物最有希望的靶标之一，因为它在病毒生命周期中发挥着关键作用。在这项研究中，通过分子对接、基于 SPR/FRET 的生物测定和诱变研究，一种名为槲皮素-3-β-半乳糖苷的天然化合物被鉴定为蛋白酶的抑制剂。分子模型和 Q189A 突变都表明 Gln189 在结合中起着关键作用。此外，实验证据表明，SARS-CoV 3CL(pro)的二级结构和酶活性不受Q189A突变的影响。在分子建模的帮助下，设计并合成了八种新的天然产物衍生物。生物测定结果揭示了新化合物构效关系的显着特征：（1）槲皮素部分7-羟基的去除降低了衍生物的生物活性；(2)糖部分的乙酰氧基化消除了抑制剂作用；(3)槲皮素7-羟基上引入大的糖取代基是可以耐受的；(4)用其他糖替代半乳糖部分不影响抑制剂效力。这项研究不仅揭示了一类新的化合物作为对抗
• Synthesis and biological evaluation of flavonoids as vasorelaxant agents
  作者：Zhiwei Chen、Yongzhou Hu、Haohao Wu、Huidi Jiang

  DOI：10.1016/j.bmcl.2004.05.061

  日期：2004.8

  Several 5,7-dihydroxyflavone and quercetin 3-O-glycosides have been synthesized and evaluated for vasorelaxant activity. A logP-activity relationship amongst flavonoids was suggested. (C) 2004 Elsevier Ltd. All rights reserved.
• WO2007/75145
  申请人：——

  公开号：——

  公开（公告）日：——
• Regio- and stereoselective synthesis of the major metabolite of quercetin, quercetin-3-O-β-d-glucuronide
  作者：Mohamed Bouktaib、Aziz Atmani、Christian Rolando

  DOI：10.1016/s0040-4039(02)01264-9

  日期：2002.8

  Protected quercetin was first transformed selectively in its 3-O-beta-D-glucoside. Further protection of the remaining phenolic hydroxyl group allows a clean oxidation of the glucoside by TEMPO/NaOCl/NaBr under phase transfer conditions into the corresponding glucuronide which was cleanly deprotected to quercetin-3-O-beta-D-glucuronide. (C) 2002 Elsevier Science Ltd. All rights reserved.
• Design, synthesis, and biological evaluation of a novel series of quercetin diacylglucosides as potent anti-MRSA and anti-VRE agents
  作者：Abugafar M.L. Hossion、Nao Otsuka、Rafiya K. Kandahary、Tomofusa Tsuchiya、Wakano Ogawa、Akimasa Iwado、Yoshito Zamami、Kenji Sasaki

  DOI：10.1016/j.bmcl.2010.02.060

  日期：2010.9

  A series of novel quercetin diacylglucosides were designed and first synthesized by Steglich esterification on the basis of MRSA strains inhibiting natural compound A. The in vitro inhibition of different multidrug resistant bacterial strains and Escherichia coli DNA gyrase B was investigated. In the series, compound 10h was up to 128-fold more potent against vancomycin-resistant enterococci and more effective than A, which represents a promising new candidate as a potent anti-MRSA and anti-VRE agent. (C) 2010 Published by Elsevier Ltd.