2-[3-(3-chloro-2,2-dimethylpropanoyloxy)-4-hydroxyphenyl]-3,5,7-trihydroxychromen-4-one | 1383562-34-2

• 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-[3-(3-chloro-2,2-dimethylpropanoyloxy)-4-hydroxyphenyl]-3,5,7-trihydroxychromen-4-one
• 英文别名: 3'-O-(3-chloropivaloyl)quercetin；2-[3-(3-Chloro-2,2-dimethylpropanoyloxy)-4-hydroxyphenyl]-3,5,7-trihydroxychromen-4-one；[2-hydroxy-5-(3,5,7-trihydroxy-4-oxochromen-2-yl)phenyl] 3-chloro-2,2-dimethylpropanoate
• CAS: 1383562-34-2
• 化学式: C₂₀H₁₇ClO₈
• 分子量: 420.803
• InChiKey: YRHRCOLNPOJQMA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  29
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  134
• 氢给体数：
  4
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  槲皮素 在 palladium 10% on activated carbon 氢气 、 potassium carbonate 、 三乙胺 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 25.0 ℃ 、415.01 kPa 条件下， 反应 36.0h， 生成 2-[3-(3-chloro-2,2-dimethylpropanoyloxy)-4-hydroxyphenyl]-3,5,7-trihydroxychromen-4-one
  参考文献：
  名称：

  Novel quercetin derivatives, their preparation, pharmaceutical compositions containing them and their use

  摘要：

  该发明涉及新型槲皮素衍生物及其药用可接受的盐、水合物、溶剂合物和二聚体；一种制备新型槲皮素衍生物及其药用可接受的盐、水合物、溶剂合物和二聚体的方法；以及包含这些物质的药物组合物，用于治疗各种疾病。槲皮素衍生物的结构由化学式I和II表示。

  公开号：

  EP2468741A1

文献信息

• [EN] QUERCETIN DERIVATIVES, THEIR PHARMACEUTICAL COMPOSITION AND USE<br/>[FR] DÉRIVÉS DE QUERCÉTINE, LEUR COMPOSITION PHARMACEUTIQUE ET LEUR UTILISATION
  申请人：USTAV EX FARMAKOLOGIE A TOXIKOLOGIE SAV

  公开号：WO2013130020A1

  公开（公告）日：2013-09-06

  The invention relates to semi-synthetic derivatives of quercetin formula I and pharmaceutically acceptable salts, hydrates and solvates, wherein groups R1 to R5, identical or different, are independently H, benzyl, and at least one group is 3-chloro-2,2-dimethylpropanoyl, 4-O-acetylferuloyl, or 2-chloro-1,4-naphthoquinon-3-yl. The invention relates to the use of derivatives of quercetin, the preparation of medicaments for the treatment or prevention of diseases or disorders where oxidative stress and polyol pathway are key etiological factors. The invention also relates to pharmaceutical compositions containing these compounds and their use in the treatment of human and animal health problems in which R1 to R5 are independently H, benzyl, and at least one group is selected from 3-chloro-2,2-dimethylpropanoyl, 4-O-acetylferuloyl, or 2-chloro-1,4-naphthoquinon-3-yl.

  该发明涉及槲皮素的半合成衍生物（化学式I）及其药用可接受的盐、水合物和溶剂化合物，其中R1至R5基团，相同或不同，独立地为H、苄基，至少一个基团为3-氯-2,2-二甲基丙酰基、4-O-乙酰基香豆酰基或2-氯-1,4-萘醌-3-基。该发明涉及槲皮素衍生物的用途，制备治疗或预防氧化应激和多醇途径是关键病因因素的疾病或紊乱的药物。该发明还涉及含有这些化合物的药物组合物及其在治疗人类和动物健康问题中的用途，其中R1至R5基团独立地为H、苄基，并且至少一个基团选自3-氯-2,2-二甲基丙酰基、4-O-乙酰基香豆酰基或2-氯-1,4-萘醌-3-基。
• 3′-O-(3-Chloropivaloyl)quercetin, α-glucosidase inhibitor with multi-targeted therapeutic potential in relation to diabetic complications
  作者：Marta Soltesova-Prnova、Ivana Milackova、Milan Stefek

  DOI：10.1515/chempap-2016-0078

  日期：2016.1.1

  of the parent quercetin. In addition, it inhibited aldose reductase isolated from rat lenses with an IC50 in the low micromolar range and attenuated sorbitol accumulation in isolated rat eye lenses with an activity comparable with that of quercetin. Moreover, it scavenged stable free-radicals of DPPH more efficiently than did quercetin. By inhibiting α-glucosidase and affecting both the polyol pathway

  槲皮素3' - O-（3-氯新戊酰基）槲皮素（CPQ）的新型衍生物以非竞争性方式抑制α-葡萄糖苷酶，其功效超过了亲本槲皮素。此外，它以低微摩尔范围的IC50抑制从大鼠晶状体分离的醛糖还原酶，并减弱了离体大鼠晶状体中山梨醇的蓄积，其活性与槲皮素相当。此外，它比槲皮素更有效地清除了DPPH的稳定自由基。通过抑制α-葡萄糖苷酶并影响多元醇途径和氧化应激，CPQ代表了糖尿病并发症多目标药理学的有前途的药物。
• Novel quercetin derivatives: synthesis and screening for anti-oxidant activity and aldose reductase inhibition
  作者：Miroslav Veverka、Ján Gallovič、Emil Švajdlenka、Eva Veverková、Naďa Prónayová、Ivana Miláčková、Milan Štefek

  DOI：10.2478/s11696-012-0240-5

  日期：2013.1.1

  The direct acylation of quercetin (I) with 3-chloro-2,2-dimethylpropanoyl chloride (II) gives a complex reaction mixture. The synthesis of different acylated quercetin with from mono- to tetra-O-substituted functions was achieved in a simple procedure wherein the yield of isomers depended on the stoichiometric ratio of reagents. The crude reaction mixtures were analysed (LC-MS) and compared with the isolated products. Unambiguous structural characterisation of isomeric quercetin derivatives was confirmed by NMR analysis. In addition, the quercetin dimer can be obtained in a high yield in the simple procedure. The anti-oxidant activity and aldose reductase inhibition of the compounds were screened with the aim of providing bi-functional remedies to treat diabetic complications and other diseases where oxidative stress and the polyol pathway are key etiological factors.

  标题：摘要 对槲皮素（I）与3-氯-2,2-二甲基丙酰氯（II）的直接酰化产生复杂的反应混合物。通过简单的程序实现了不同酰化槲皮素的合成，从单取代到四取代功能，产物的收率取决于试剂的化学计量比。原始反应混合物经过（液相色谱-质谱）分析，并与分离的产物进行比较。通过NMR分析确认了异构槲皮素衍生物的结构特征。此外，在简单的程序中可以高产率地得到槲皮素二聚体。通过筛选这些化合物的抗氧化活性和醛糖还原酶抑制作用，旨在提供治疗糖尿病并发症和其他疾病的双重功能疗法，其中氧化应激和多元醇途径是关键的病因因素。
• Novel quercetin derivatives, their preparation, pharmaceutical compositions containing them and their use
  申请人：Bel/Novamann International s.r.o.

  公开号：EP2468741A1

  公开（公告）日：2012-06-27

  The invention relates to novel quercetin derivatives and pharmaceutically acceptable salts, hydrates, and solvates and dimers thereof; a process for the preparation of the novel quercetin derivatives and pharmaceutically acceptable salts, hydrates, and solvates and dimers thereof; and pharmaceutical compositions comprising the same that are useful for the treatment of various disorders. The quercetin derivatives are shown by formula I and II.

  该发明涉及新型槲皮素衍生物及其药用可接受的盐、水合物、溶剂合物和二聚体；一种制备新型槲皮素衍生物及其药用可接受的盐、水合物、溶剂合物和二聚体的方法；以及包含这些物质的药物组合物，用于治疗各种疾病。槲皮素衍生物的结构由化学式I和II表示。