104691-86-3

Usage

Uses

Used in Pharmaceutical Applications:
8-PRENYLGENISTEIN is used as a bioactive compound for its inhibitory activity against tyrosine kinases, including the autophosphorylation of epidermal growth factor receptor kinase. This property makes it a potential therapeutic agent for various diseases, including cancer. It also inhibits other protein kinases through competitive inhibition of ATP, leading to cell-cycle arrest and apoptosis in certain cancer cell lines.
Used in Cosmetic Applications:
8-PRENYLGENISTEIN is used as an active ingredient in the cosmetic industry for its potential anti-aging and skin protective properties. Its ability to inhibit certain enzymes and modulate cellular processes may contribute to improved skin health and appearance.
Used in Research Applications:
8-PRENYLGENISTEIN is also used as a research tool for studying the mechanisms of various biological processes, such as cell signaling, cell proliferation, and apoptosis. Its unique chemical structure and biological activities make it a valuable compound for understanding the complex interactions within cellular systems.

InChI:InChI=1/C20H18O5/c1-11(2)3-8-14-16(22)9-17(23)18-19(24)15(10-25-20(14)18)12-4-6-13(21)7-5-12/h3-7,9-10,21-23H,8H2,1-2H3

Upstream product

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• 556-82-1 3-methyl-2-buten-1-ol 
• 210166-27-1 Acetic acid 3,5-bis-benzyloxy-2-[2-(4-benzyloxy-phenyl)-3,3-dimethoxy-propionyl]-6-iodo-phenyl ester 
• 210166-30-6 4',5,7-tris(benzoyloxy)-8-(3-hydroxy-3-methylbutyl)isoflavone 
• 210166-29-3 5,7-Bis-benzyloxy-3-(4-benzyloxy-phenyl)-8-(3-hydroxy-3-methyl-but-1-ynyl)-chromen-4-one 
• 210166-26-0 Acetic acid 3,5-bis-benzyloxy-2-[(E)-3-(4-benzyloxy-phenyl)-acryloyl]-6-iodo-phenyl ester 
• 210166-28-2 5,7-Bis-benzyloxy-3-(4-benzyloxy-phenyl)-8-iodo-chromen-4-one 
• 210166-25-9 (E)-3-(4-Benzyloxy-phenyl)-1-(4,6-bis-benzyloxy-2-hydroxy-3-iodo-phenyl)-propenone 
• 160154-81-4 4',6'-bis(benzyloxy)-3'-iodo-2'-(methoxymethoxy)acetophenone 
• 104691-92-1 lupiwighteone hydrate 
• 95165-66-5 3-Iod-2-hydroxy-4,6-dibenzyloxy-acetophenon 
• 18065-05-9 1-[2,4-bis(benzyloxy)-6-hydroxyphenyl]ethanone 
• 583037-95-0 4-(7-acetyloxy-5-((3-methylbut-2-en-l-yl))-4-oxo-4H-chromen-3-yl)phenyl acetate 
• 65388-04-7 4-(7-acetoxy-5-hydroxy-4-oxo-4H-chromen-3-yl)phenyl acetate 

Downstream Products

• 76166-59-1 atalantoflavone 

Relevant academic research and scientific papers

Induction of enantio-selective apoptosis in human leukemia HL-60 cells by (S)-erypoegin K, an isoflavone isolated from Erythrina poeppigiana

Erypoegin K, an isoflavone isolated from the stem bark of Erythrina poeppigiana, has potent apoptosis-inducing effect on human leukemia HL-60 cells. Erypoegin K has a chiral carbon at the C-2′′ position of its furan ring and naturally occurs as a racemic mixture of (S)- and (R)-isomers. In the present study, we semi-synthesized (RS)-erypoegin K from genistein and separated the optical isomers by HPLC using a chiral column to characterize its apoptosis-inducing activity. Apoptotic cell death was assessed by analyzing caspase-3 and caspase-9 activation, nuclear fragmentation, and genomic DNA ladder formation. (S)-erypoegin K showed exclusive anti-proliferative and apoptosis-inducing activity, with an IC50 value of 90 nM, about 50% lower than that of its racemic mixture (175 nM). By contrast, no apoptosis-inducing activity was shown by the (R)-isomer. In addition, methylglyoxal accumulation in the culture medium was observed only in cells treated with (S)-erypoegin K. These results demonstrated that (S)-erypoegin K is a unique bioactive component that has potent apoptosis-inducing activity on HL-60 cells.

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.

GLYOXALASE I INHIBITOR AND USE THEREOF

PROBLEM TO BE SOLVED: To provide a glyoxalase I inhibitor that is a compound showing antitumor activity. SOLUTION: The present invention provides a glyoxalase I inhibitor comprising a compound represented by the following formula, and an antitumor agent. SELECTED DRAWING: None COPYRIGHT: (C)2017,JPOandINPIT

Synthesis, α-glucosidase inhibitory and molecular docking studies of prenylated and geranylated flavones, isoflavones and chalcones

Three series of prenylated and/or geranylated flavonoids were synthesized and evaluated for their α-glucosidase inhibitory activity. The 3′,5′-digeranylated chalcone (16) was identified as a new α-glucosidase inhibitor whose activity (IC50 = 0.

Anti-AGEs and antiparasitic activity of an original prenylated isoflavonoid and flavanones isolated from Derris ferruginea

A new isoflavonoid, 5-hydroxy-3-(4-hydroxyphenyl)-8-isopropenyl-8,9- dihydro-4H-furo-[2,3-h]-chromen-4-one named derrisisoflavone G (1), four known prenylated flavanones (2-5), four known isoflavonoids (6-9) and two phenolic derivatives (10, 11) have been

SYNTHESIS OF 13C-LABELLED ESTROGEN ANALOGUES

There is provided a method of producing novel 13C-labelled estrogen analogues. The method preferably proceeds via an intermediate A or B or which is a mixture of (A) or (B): wherein a13C atom is located at one or more of positions 1, 2, 3 or 4 and wherein R is an optionally substituted alkane, alkene, alkyne or aryl group. Preferably R is -CH2Ph. An alternative preferred intermediate compound is 13C-resorcinol.

Synthesis of lupiwighteone via a para-Claisen-Cope rearrangement

The lanthanide catalysed para-Claisen-Cope rearrangement has been used as the key step in a short synthesis of the prenylated isoflavone, lupiwighteone. The Mitsunobu reaction was employed for the 5-O-prenylation of the acid/base sensitive acetylated isof

Regioselective Synthesis of Prenylisoflavones. Syntheses of Lupiwighteone, Lupiwighteone Hydrate and Related Compounds

The palladium-catalyzed coupling reaction of 4',5.7-tris(benzyloxy)-8-iodoisoflavone 11, synthesized from the 3'-iodochalcone 8, with 2-methyl-3-butyn-2-ol gave the corresponding 8-(3-hydroxy-3-methylbutynyl)isoflavone 12.Catalytic hydrogenation of 12 gav