Research Progress on the Synthesis of Quercetin Derivatives

doi:10.6023/cjoc202203016

Abstract

Quercetin, as a natural antioxidant, is mainly found in vegetables, fruits and other plants. It can regulate many intracellular and extracellular signaling pathways related to disease progression. It can be anti-inflammatory, antiviral, anticancer, prevention and treatment of cardiovascular and cerebrovascular diseases, thus has a wide range of pharmacological activities. Due to the structural characteristics of quercetin, its low bioavailability limits its clinical application. However, the low molecular mass and easily modifiable chemical groups of quercetin make it attractive for drug development. Therefore, researchers have designed and synthesized new quercetin derivatives through various methods to improve its unfavorable factors. Many quercetin derivatives with excellent properties, good solubility, high bioavailability, stable metabolism, low toxicity and significant biological activity have been synthesized. The recent progress in the synthesis of quercetin derivatives and their biological activities is reviewed, providing a reference for the further development of quercetin derivatives.

Key words: quercetin, derivative, synthesis, antioxidant, anticancer, biological activity

Cite this article

Yajun Mao, Xiangmin Shao, Yangjie Li, Ruimei Cao, Yali Feng, Guangyu Zhai. Research Progress on the Synthesis of Quercetin Derivatives[J]. Chinese Journal of Organic Chemistry, 2022, 42(11): 3588-3605.

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Fig. & Tab. 22

Figure 1. Structure and modification of quercetin

Scheme 1. Synthesis of quercetin-3-O- or 7-O-amino acid derivatives

Scheme 2. Synthesis of quercetin-3-O-amino acid ester derivatives

Scheme 3. Synthesis of quercetin-5-acyl ester

Scheme 4. Synthesis of quercetin-3-O-benzoate derivatives

Scheme 5. Synthesis of quercetin lipoate

Scheme 6. Synthesis of quercetin phosphate

Scheme 7. Synthesis of quercetin sulfate

Scheme 8. Synthesis of quercetin tetramethyl alkyl amino ether

Scheme 9. Synthesis of quercetin 5, or 3'-ether acetic acid derivatives

Scheme 10. Synthesis of quercetin-3-O-acetamide derivatives

Scheme11. Synthesis of quercetin-3-propyl ether

Scheme 12. Synthesis of quercetin derivatives containing 1,4-pentadien-3-one

Scheme 13. Synthesis of quercetin-3-ethyl ether derivatives

Scheme 14. Synthesis of quercetin-8-methylamino derivatives

Scheme 15. Synthesis of C-8 isopentenyl quercetin

Scheme 16. Synthesis of C-5' isopentenyl quercetin

Scheme 17. Synthesis of 8-aryl pentamethyl quercetin derivatives

Scheme 18. Synthesis of quercetin carbonyl derivatives

Scheme 19. Synthesis of quercetin carbonyl oxygen substituted by sulfur or selenium derivatives

Scheme 20. Synthesis of quercetin metal complex

Figure 2. More active quercetin derivatives

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