2-((2-(3,4-dihydroxyphenyl)-3,5-dihydroxy-4-oxo-4H-chromen-7-yl)oxy)acetic acid | 1144104-76-6

• 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-(3,4-dihydroxyphenyl)-3,5-dihydroxy-4-oxo-4H-chromen-7-yl)oxy)acetic acid
• 英文别名: 7-O-(hydroxycarbonyl)methylquercetin；2-[2-(3,4-Dihydroxyphenyl)-3,5-dihydroxy-4-oxochromen-7-yl]oxyacetic acid
• CAS: 1144104-76-6
• 化学式: C₁₇H₁₂O₉
• 分子量: 360.277
• InChiKey: YIAXTIPXNTWVKY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  26
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  154
• 氢给体数：
  5
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  2-((2-(3,4-dihydroxyphenyl)-3,5-dihydroxy-4-oxo-4H-chromen-7-yl)oxy)acetic acid 在 氯化亚砜 作用下， 生成
  参考文献：
  名称：

  一种葡聚糖-槲皮素前药聚合物的制备方法

  摘要：

  本发明属于前药载体制备技术领域，公开了一种葡聚糖‑槲皮素前药聚合物的制备方法。该制备方法通过对槲皮素的羟基进行保护、选择性取代、脱保护、酰氯化等反应，引入酰氯基团，再将其与葡聚糖连接，制备葡聚糖‑槲皮素前药聚合物，该制备方法方便易行，反应条件温和。本发明为对槲皮素的衍生物进行研究构建理想的药物载体来改善其水溶性提供了基础，为提高生物利用度提供了前期方案。

  公开号：

  CN110279869B
• 作为产物：
  描述：

  槲皮素 在 吡啶 、 咪唑 、 盐酸 、 caesium carbonate 作用下， 以 水 、 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 反应 10.5h， 生成 2-((2-(3,4-dihydroxyphenyl)-3,5-dihydroxy-4-oxo-4H-chromen-7-yl)oxy)acetic acid
  参考文献：
  名称：

  Silica particles with a quercetin–R5 peptide conjugate are taken up into HT-29 cells and translocate into the nucleus

  摘要：

  通过生物仿生硅沉淀和槲皮素-R5肽生成的颗粒进入HT-29细胞核，而不会引起毒性。

  DOI：

  10.1039/c9cc02215e

文献信息

• Flavonols
  申请人：The University of Melbourne

  公开号：US07863323B1

  公开（公告）日：2011-01-04

  A compound of the formula (I): wherein R is selected from the group consisting of H, alkyl, alkenyl, alkynyl, heteroalkyl, cycloalkyl, heterocycloalkyl, aryl, heteroaryl and acyl, each of which may be optionally substituted; R1 is an organic moiety that is capable of being converted into a charged group; each X and Y is independently selected from the group consisting of H, halogen, —CN, —NO2, —CF3, —OCF3, alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, heteroalkyl, cycloalkyl, cycloalkenyl, heterocycloalkyl, heterocycloalkenyl, aryl, heteroaryl, cycloalkylalkyl, heterocycloalkylalkyl, arylalkyl, heteroarylalkyl, arylalkenyl, cycloalkylheteroalkyl, arylheteroalkyl, heterocycloalkylheteroalkyl, heteroarylheteroalkyl, hydroxy, hydroxyalkyl, alkoxy, alkoxyalkyl, alkoxyaryl, alkenyloxy, alkynyloxy, cycloalkyloxy, heterocycloalkyloxy, aryloxy, heteroaryloxy, arylalkyloxy, phenoxy, benzyloxy, amino, alkylamino, aminoalkyl, acylamino, arylamino, sulfonylamino, sulfinylamino, —COOH, —COR2, —COOR2, —CONHR2, —NHCOR2, —NHCOOR2, —NHCONHR2, C(═NOH)R2, alkoxycarbonyl, alkylaminocarbonyl, sulfonyl, alkylsulfonyl, alkylsulfinyl, arylsulfonyl, arylsulfinyl, aminosulfonyl, SR2 and acyl, each of which may be optionally substituted; each R2 is independently selected from the group consisting of H, alkyl, alkenyl, alkynyl, haloalkyl, heteroalkyl, cycloalkyl, heterocycloalkyl, aryl, heteroaryl, cycloalkylalkyl, heterocycloalkylalkyl, arylalkyl, heteroarylalkyl, and acyl, each of which may be optionally substituted; m is an integer selected from the group consisting of 0, 1, 2, 3, 4 and 5; p is an integer selected from 0, 1, 2 and 3; or a pharmaceutically acceptable salt or prodrug thereof.

  公式（I）的化合物：其中R从H、烷基、烯基、炔基、杂原子烷基、环烷基、杂环烷基、芳基、杂芳基和酰基组成的群中选择，每个都可以选择性地被取代；R1是一个有能力转化为带电基团的有机基团；每个X和Y分别从H、卤素、—CN、—NO2、—CF3、—OCF3、烷基、烯基、炔基、卤代烷基、卤代烯基、杂原子烷基、环烷基、环烯基、杂环烷基、杂环烯基、芳基、杂芳基、环烷基烷基、杂环烷基烷基、芳基烷基、杂芳基烷基、芳基烯基、环烷基杂原子烷基、芳基杂原子烷基、杂环烷基杂原子烷基、杂芳基杂原子烷基、羟基、羟基烷基、烷氧基、烷氧基烷基、烷氧基芳基、烯基氧基、炔基氧基、环烷氧基、杂环烷氧基、芳氧基、杂芳氧基、芳基烷氧基、苯氧基、苄氧基、氨基、烷基氨基、氨基烷基、酰氨基、芳基氨基、磺酰氨基、亚砜氨基、—COOH、—COR2、—COOR2、—CONHR2、—NHCOR2、—NHCOOR2、—NHCONHR2、C(═NOH)R2、烷氧羰基、烷基氨基羰基、磺酰基、烷基磺酰基、烷基亚砜基、芳基磺酰基、芳基亚砜基、氨基磺酰基、SR2和酰基组成的群中选择，每个都可以选择性地被取代；每个R2从H、烷基、烯基、炔基、卤代烷基、杂原子烷基、环烷基、杂环烷基、芳基、杂芳基、环烷基烷基、杂环烷基烷基、芳基烷基、杂芳基烷基和酰基组成的群中选择，每个都可以选择性地被取代；m是从0、1、2、3、4和5中选择的整数；p是从0、1、2和3中选择的整数；或其药用盐或前药。
• [EN] POLYPHENOL-PEPTIDE CONJUGATES FOR NUCLEAR-TARGETED DELIVERY<br/>[FR] CONJUGUÉS POLYPHÉNOL-PEPTIDE POUR L'ADMINISTRATION CIBLANT LE NOYAU
  申请人：UNIV WIEN

  公开号：WO2020136240A1

  公开（公告）日：2020-07-02

  The present invention relates to a polyphenol-peptide conjugate composed of: (i) a peptide comprising the amino acid sequence Arg-Arg-X1-Leu, wherein X1 refers to one or two hydrophobic amino acids selected independently from lie, Leu, Val, Phe, Trp, and Met; (ii) at least one polyphenol which is covalently bound to the peptide; and (iii) optionally at least one cargo which, if present, is covalently bound to the peptide. The polyphenol-peptide conjugate can be encapsulated with silica. The invention thus also provides silica particles comprising the polyphenol-peptide conjugate encapsulated by a silica shell. The silica particles allow the efficient cellular uptake and targeted delivery of the polyphenol-peptide conjugate into the cell nucleus, and can therefore advantageously be used for nuclear-targeted gene or drug delivery.

  本发明涉及一种由以下组成的多酚-肽共轭物：（i）包括氨基酸序列Arg-Arg-X1-Leu的肽，其中X1是从lie、Leu、Val、Phe、Trp和Met中独立选择的一个或两个疏水性氨基酸；（ii）至少一种共价结合到肽上的多酚；以及（iii）可选地，至少一种共价结合到肽上的载荷。多酚-肽共轭物可以被硅化物封装。因此，本发明还提供了由硅壳封装的多酚-肽共轭物的硅颗粒。硅颗粒能够有效地被细胞摄取并定向传递到细胞核中，因此可以有利地用于核靶向基因或药物传递。
• Inhibition of Heat Shock Induction of Heat Shock Protein 70 and Enhancement of Heat Shock Protein 27 Phosphorylation by Quercetin Derivatives
  作者：Rongsheng E. Wang、Jeffrey L.-F. Kao、Carolyn A. Hilliard、Raj K. Pandita、Joseph L. Roti Roti、Clayton R. Hunt、John-Stephen Taylor

  DOI：10.1021/jm801445c

  日期：2009.4.9

  Inhibitors of heat-induced heat shock protein 70 (HSP70) expression have the potential to enhance the therapeutic effectiveness of heat-induced radiosensitization of tumors. Among known small molecule inhibitors, quercetin has the advantage of being easily modified for structure-activity studies. Herein, we report the ability of five monomethyl and five carbomethoxymethyl derivatives of quercetin to inhibit heat-induced HSP70 expression and enhance HSP27 phosphorylation in human cells. While quercetin and several derivatives inhibit HSP70 induction and enhance HSP27 phosphorylation at Ser78, other analogues selectively inhibit HSP70 induction without enhancing HSP27 phosphorylation that would otherwise aid in cell survival. We also show that good inhibitors of HSP70 induction are also good inhibitors of both CK2 and CamKII, kinases that are known to activate HSP70 expression by phosphorylation of heat shock transcription factor 1. Derivatives that show poor inhibition of either or both kinases are not good inhibitors of HSP70 induction, suggesting that quercetin's effectiveness is due to its ability to inhibit both kinases.
• US7863323B1
  申请人：——

  公开号：US7863323B1

  公开（公告）日：2011-01-04
• Silica particles with a quercetin–R5 peptide conjugate are taken up into HT-29 cells and translocate into the nucleus
  作者：Giorgia Del Favero、Friedrich Bialas、Stephanie Grabher、Anja Wittig、Birgit Bräuer、Dagmar Gerthsen、Cécile Echalier、Meder Kamalov、Doris Marko、Christian F. W. Becker

  DOI：10.1039/c9cc02215e

  日期：——

  Particles generated by biomimetic silica precipitation with a quercetin–R5 peptide enter the nucleus of HT-29 cells without inducing toxicity.

  通过生物仿生硅沉淀和槲皮素-R5肽生成的颗粒进入HT-29细胞核，而不会引起毒性。