34125-75-2

Upstream product

• 115-18-4 2-methyl-3-buten-2-ol 
• 480-40-0 5,7-dihydroxy-2-phenyl-chromen-4-one 
• 870-63-3 prenyl bromide 
• 358-72-5 dimethylallyl diphosphate 
• 556-82-1 3-methyl-2-buten-1-ol 
• 447451-03-8 7-(tert-butyl-diphenyl-silanyloxy)-5-hydroxy-2-phenyl-chromen-4-one 
• 447451-04-9 7-(tert-butyl-diphenyl-silanyloxy)-5-(3-methyl-but-2-enyloxy)-2-phenyl-chromen-4-one 
• 375373-63-0 5-hydroxy-7-(2-methoxy-ethoxymethoxy)-8-(3-methyl-but-2-enyl)-2-phenyl-chromen-4-one 

Downstream Products

• 270563-47-8 2-cyclohexyl-5,7-dihydroxy-8-(3-methylbutyl)chromone 

Relevant academic research and scientific papers

Prenylated flavonoids with potential antimicrobial activity: Synthesis, biological activity, and in silico study

Prenylated flavonoids are an important class of naturally occurring flavonoids with important biological activity, but their low abundance in nature limits their application in medicines. Here, we showed the hemisynthesis and the determination of various biological activities of seven prenylated flavonoids, named 7–13, with an emphasis on antimicrobial ones. Compounds 9, 11, and 12 showed inhibitory activity against human pathogenic fungi. Compounds 11, 12 (flavanones) and 13 (isoflavone) were the most active against clinical isolated Staphylococcus aureus MRSA, showing that structural requirements as prenylation at position C-6 or C-8 and OH at positions C-5, 7, and 4′ are key to the antibacterial activity. The combination of 11 or 12 with commercial antibiotics synergistically enhanced the antibacterial activity of vancomycin, ciprofloxacin, and methicillin in a factor of 10 to 100 times against drug-resistant bacteria. Compound 11 combined with ciprofloxacin was able to decrease the levels of ROS generated by ciprofloxacin. According to docking results of S enantiomer of 11 with ATP-binding cassette transporter showed the most favorable binding energy; however, more studies are needed to support this result.

Regio- and stereospecific prenylation of flavonoids by Sophora flavescens prenyltransferase

Prenylflavonoids are valuable natural products that are widely distributed in plants. They often possess divergent biological properties, including phytoestrogenic, anti-bacterial, anti-tumor, and anti-diabetic activities. The reaction catalyzed by prenyltransferases represents a Friedel-Crafts alkylation of the flavonoid skeleton in the biosynthesis of natural prenylflavonoids and often contributes to the structural diversity and biological activity of these compounds. However, only a few plant flavonoid prenyltransferases have been identified thus far, and these prenyltransferases exhibit strict substrate specificity and low catalytic efficiency. In this article, a flavonoid prenyltransferase from Sophora flavescens, SfFPT, has been identified that displays high catalytic efficiency with high regiospecificity acting on C-8 of structurally different types of flavonoid (i.e., flavanone, flavone, flavanonol, and dihydrochalcone, etc.). Furthermore, SfPFT exhibits strict stereospecificity for levorotatory flavanones to produce (2S)-prenylflavanones. This study is the first to demonstrate the substrate promiscuity and stereospecificity of a plant flavonoid prenyltransferase in vitro. Given its substrate promiscuity and high catalytic efficiency, SfFPT can be used as an environmentally friendly and efficient biological catalyst for the regio- and stereospecific prenylation of flavonoids to produce bioactive compounds for potential therapeutic applications. Copyright

Regioselective syntheses of 6-(1,1-dimethylallyl)- and 8-(3,3-dimethylallyl) chrysins

The first regioselective syntheses of 6-(1,1-dimethylallyl)- and 8-(3,3-dimethylallyl) chrysins have been designed. Claisen rearrangement of protected 5-O-(3,3-dimethylallyl) chrysin in N,N-diethylaniline at 200-217°C gave selective access to the 8-(3,3-dimethylallyl) isomer. Similar rearrangement in N,N-diethylbutylamine at 140-160°C, or in cycloheptane/Eu(fod)3 at 100°C, led to the formation of the 6-(1,1-dimethylallyl) isomer. Four different protecting groups for position 7 of chrysin have been compared, and found to follow the order of interest Bz>MOM>TBDPS>MEM.

C-isoprenylation of flavonoids enhances binding affinity toward P-glycoprotein and modulation of cancer cell chemoresistance

Previous studies have shown that flavones bind to P-glycoprotein (Pgp) with higher affinity than isoflavones, flavanones, and glycosylated derivatives. In the present work, a series of C- or O-substituted hydrophobic derivatives of chrysin were synthesized to further investigate structural requirements of the A ring toward Pgp modulation. Increasing hydrophobicity at either position 6, 8, or 7 increased the affinity of in vitro binding to a purified cytosolic domain of Pgp, but only benzyl and 3,3-dimethylallyl C-substitution produced a high maximal quenching of the protein intrinsic fluorescence. Inhibition of membrane Pgp within leukemic cells, characterized by intracellular drug accumulation, was specifically produced by isoprenylated derivatives, with 8-(3,3-dimethylallyl)chrysin being even more efficient than the commonly used cyclosporin A.

Mechanism on one-sided Wessely-Moser rearrangement reaction

Wessely-Moser rearrangement reaction of 5,7-dihydroxychromone derivatives with an isopentyl side chain at C-6 or C-8 position was examined. All reactions gave 8-isopentylchromone derivative predominantly as rearrangement product. Kinetic analysis of the o