2255-62-1

Usage

Uses

Used in Pharmaceutical Industry:
5,7-Dihydroxy-6-(1-methyl-2-pyrrolidinyl)flavone is used as a pharmaceutical compound for its potential therapeutic applications. The presence of hydroxy and carboxy groups in its structure allows for interactions with biopolymers and macromolecules, making it a promising candidate for drug development.
Used in Chemical Research:
This alkaloid is also utilized in chemical research for studying its structure, properties, and potential reactions with other compounds. Understanding its behavior can lead to the discovery of new applications and uses in various fields.
Used in Natural Product Analysis:
5,7-Dihydroxy-6-(1-methyl-2-pyrrolidinyl)flavone serves as a marker compound in the analysis of natural products derived from Ficus pantoniana King. Its presence can help identify and characterize the plant's chemical composition and potential biological activities.

References

Johns, Russel, Hefferman., Tetrahedron Lett., 1987 (1965)

InChI:InChI=1/C20H19NO4/c1-21-9-5-8-13(21)18-14(22)11-17-19(20(18)24)15(23)10-16(25-17)12-6-3-2-4-7-12/h2-4,6-7,10-11,13,22,24H,5,8-9H2,1H3

Upstream product

• 7225-08-3 2-hydroxy-1-methylpyrrolidine 
• 480-40-0 5,7-dihydroxy-2-phenyl-chromen-4-one 

Relevant academic research and scientific papers

Synthesis, biological evaluation, and molecular modeling of natural and unnatural flavonoidal alkaloids, inhibitors of kinases

The screening of the ICSN chemical library on various disease-relevant protein kinases led to the identification of natural flavonoidal alkaloids of unknown configuration as potent inhibitors of the CDK1 and CDK5 kinases. We thus developed an efficient and modular synthetic strategy for their preparation and that of analogues in order to determine the absolute configuration of the active natural flavonoidal alkaloids and to provide further insights on the structure-activity relationships in this series. The structural determinants of the interaction between some flavonoidal alkaloids with specific kinases were also evaluated using molecular modeling.

An efficient one-step synthesis of piperidin-2-yl and pyrrolidin-2-yl flavonoid alkaloids through phenolic Mannich reactions

An efficient one-step synthesis of piperidin-2-yl and pyrrolidin-2-yl flavonoid alkaloids was achieved in good to excellent yields by a highly regioselective phenolic Mannich reaction of chrysin with cyclic imines or iminium salts. Performing the reaction in a mixture of H2O/THF in the absence of an external reagent afforded the C-6 alkylated product exclusively. The same reaction in water in the presence of NaOH provided the C-8 alkylated flavonoid as a major product. The reaction has been successfully extended to simple phenols.