3,7-bis(benzyloxy)-2-(3,4-dihydroxyphenyl)-5-hydroxy-4H-chromen-4-one | 498548-15-5

• 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: 3,7-bis(benzyloxy)-2-(3,4-dihydroxyphenyl)-5-hydroxy-4H-chromen-4-one
• 英文别名: 2-(3,4-Dihydroxyphenyl)-5-hydroxy-3,7-bis(phenylmethoxy)chromen-4-one
• CAS: 498548-15-5
• 化学式: C₂₉H₂₂O₇
• 分子量: 482.489
• InChiKey: SUWZRJNANIQBFX-UHFFFAOYSA-N

物化性质

• 沸点：
  773.6±60.0 °C(Predicted)
• 密度：
  1.46±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  36
• 可旋转键数：
  7
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  105
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  3,7-bis(benzyloxy)-2-(3,4-dihydroxyphenyl)-5-hydroxy-4H-chromen-4-one 在 20 % Pd(OH)2/C 、 氢气 、 sodium methylate 、 potassium carbonate 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 30.5h， 生成 绣线菊甙
  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：

  槲皮素 在 盐酸 、 水 、 potassium carbonate 作用下， 以 乙醇 、 二乙二醇二甲醚 、 N,N-二甲基甲酰胺 为溶剂， 反应 10.0h， 生成 3,7-bis(benzyloxy)-2-(3,4-dihydroxyphenyl)-5-hydroxy-4H-chromen-4-one
  参考文献：
  名称：

  N-乙酰氨基葡萄糖的三种槲皮素O-β-葡萄糖苷的区域特异性合成

  摘要：

  N-乙酰氨基葡萄糖的三种槲皮素O-β-葡萄糖苷的区域特异性合成已以良好的收率实现。槲皮素的选择性二和三 O-苄基化，然后在相转移催化条件下与 2-乙酰氨基-3,4,6-三-O-乙酰基-2-脱氧-α-D-吡喃葡萄糖基氯进行 O-糖基化，得到，经过去乙酰化和去苄基化后，3-、3'-和 4'-糖基化槲皮素。

  DOI：

  10.3184/174751918x15232706115112

文献信息

• 槲皮素衍生物及其制备方法和应用
  申请人：南京惠特莱医药科技有限公司

  公开号：CN104557891B

  公开（公告）日：2017-12-19

  本发明公开了一种槲皮素的衍生物及其制备方法和应用，该制备方法首先用二氯二苯基甲烷保护槲皮素邻二酚羟基，并结合苄基保护基，得到选择性保护的槲皮素衍生物，再分别单独与硫酸二甲酯、硫酸二乙酯、烯丙基溴、对甲苯磺酰氯和乙酸酐进行反应，生成相应的槲皮素衍生物。所制备的衍生化合物都表现出优于槲皮素的抑制NRK‑49F增殖活性。其中，甲基和对甲苯磺酰基复合取代的槲皮素衍生物20a‑1、14a‑2和23d‑1表现出更加优良的抑制NRK‑49F增殖活性，抑制率分别达到86.33%、78.04%、75.91%。可见，目前得到的槲皮素衍生化产物对肾成纤维细胞NRK‑49F增殖有明显的抑制作用。
• Glucuronidation of Methylated Quercetin Derivatives: Chemical and Biochemical Approaches
  作者：Maite L. Docampo-Palacios、Anislay Alvarez-Hernández、Olubu Adiji、Daylin Gamiotea-Turro、Alexander B. Valerino-Diaz、Luís P. Viegas、Ikenna E. Ndukwe、Ângelo de Fátima、Christian Heiss、Parastoo Azadi、Giulio M. Pasinetti、Richard A. Dixon

  DOI：10.1021/acs.jafc.0c04500

  日期：2020.12.16

  Botanical supplements derived from grapes are functional in animal model systems for the amelioration of neurological conditions, including cognitive impairment. Rats fed with grape extracts accumulate 3′-O-methyl-quercetin-3-O-β-d-glucuronide (3) in their brains, suggesting 3 as a potential therapeutic agent. To develop methods for the synthesis of 3 and the related 4′-O-methyl-quercetin-7-O-β-d-glucuronide

  源自葡萄的植物补充剂在动物模型系统中具有改善神经系统疾病（包括认知障碍）的功能。喂食葡萄提取物的大鼠大脑中会积聚 3′- O - 甲基 - 槲皮素 - 3 - O -β - d -葡萄糖醛酸苷 ( 3 )，表明3是一种潜在的治疗剂。开发3及相关4′ - O-甲基-槲皮素-7- O -β- d-葡萄糖醛酸苷( 4 )、3- O-甲基-槲皮素-3′- O -β- d-的合成方法葡萄糖醛酸苷 ( 5 ) 和 4′- O -甲基-槲皮素-3′- O -β- d -葡萄糖醛酸苷 ( 6 ) 在大脑中不存在，我们评估了酶法半合成和全化学合成方法。哺乳动物UDP-葡萄糖醛酸基转移酶的生物催化从4'- O-甲基槲皮素产生多种葡萄糖醛酸化产物，但不具有成本效益。另一方面，化学合成方法提供了良好的结果；3、5和6分六步合成，总产率分别为12%、18%和30%，而4分五步合成，总产率34%。还提出了在槲皮素葡萄
• 케르세틴 유도체, 이를 포함하는 암 예방 또는 치료용 약학적 조성물 및 이의 합성 방법
  申请人：DAEGU CATHOLIC UNIVERSITY INDUSTRY ACADEMIC COOPERATION FOUNDATION 대구가톨릭대학교산학협력단(220070042373) BRN ▼515-82-06711

  公开号：KR20210004643A

  公开（公告）日：2021-01-13

  본 발명은 케르세틴의 4'-히드록시기가 치환된 신규 케르세틴 유도체, 이를 포함하는 암 예방 또는 치료용 약학적 조성물 및 이의 합성 방법에 관한 것이다.

  本发明涉及一种取代了4'-羟基的新型槲皮素衍生物，包括含有该衍生物的用于癌症预防或治疗的药学组合物，以及其合成方法。
• Design and discovery of flavonoid-based HIV-1 integrase inhibitors targeting both the active site and the interaction with LEDGF/p75
  作者：Bo-Wen Li、Feng-Hua Zhang、Erik Serrao、Huan Chen、Tino W. Sanchez、Liu-Meng Yang、Nouri Neamati、Yong-Tang Zheng、Hui Wang、Ya-Qiu Long

  DOI：10.1016/j.bmc.2014.04.016

  日期：2014.6

  HIV integrase (IN) is an essential enzyme for the viral replication. Currently, three IN inhibitors have been approved for treating HIV-1 infection. All three drugs selectively inhibit the strand transfer reaction by chelating a divalent metal ion in the enzyme active site. Flavonoids are a well-known class of natural products endowed with versatile biological activities. Their beta-ketoenol or catechol structures can serve as a metal chelation motif and be exploited for the design of novel IN inhibitors. Using the metal chelation as a common pharmacophore, we introduced appropriate hydrophobic moieties into the flavonol core to design natural product-based novel IN inhibitors. We developed selective and efficient syntheses to generate a series of mono 3/5/7/3'/4'-substituted flavonoid derivatives. Most of these new compounds showed excellent HIV-1 IN inhibitory activity in enzyme-based assays and protected against HIV-1 infection in cell-based assays. The 7-morpholino substituted 7c showed effective antiviral activity (EC50 = 0.826 mu g/mL) and high therapeutic index (TI > 242). More significantly, these hydroxyflavones block the IN-LEDGF/p75 interaction with low-to sub-micromolar IC50 values and represent a novel scaffold to design new generation of drugs simultaneously targeting the catalytic site as well as protein-protein interaction domains. (C) 2014 Elsevier Ltd. All rights reserved.
• Hemisynthesis of all the O-monomethylated analogues of quercetin including the major metabolites, through selective protection of phenolic functions
  作者：Mohamed Bouktaib、Stéphane Lebrun、Aziz Atmani、Christian Rolando

  DOI：10.1016/s0040-4020(02)01306-6

  日期：2002.12

  A new methodology for the hemisynthesis of all the five O-monomethylated analogues of quercetin (3'-O-methylquercetin (isorhamnetin), 4'-O-methylquercetin (tamarixetin), 3-O-methylquercetin, 5-O-methylquercetin (azaleatin) and 7-O-methylquercetin (rhamnetin)) through sequential protection of the different phenolic functions of quercetin is reported. (C) 2002 Published by Elsevier Science Ltd.