14917-41-0

Usage

Uses

Used in Pharmaceutical Development:
2',4',6',3,4-Pentahydroxychalcone is used as a key component in the development of new pharmaceutical drugs due to its diverse range of biological activities and potential therapeutic benefits.
Used in Anticancer Applications:
In the field of oncology, 2',4',6',3,4-Pentahydroxychalcone is used as an anticancer agent, exhibiting potential effects against various types of cancer. Its mechanism of action involves modulation of multiple signaling pathways, which can lead to the inhibition of tumor growth and progression.
Used in Anti-diabetic Applications:
2',4',6',3,4-Pentahydroxychalcone is utilized as an anti-diabetic agent, where it may help in managing and treating diabetes by targeting specific metabolic pathways and improving insulin sensitivity.
Used in Anti-inflammatory Applications:
In the context of inflammation, 2',4',6',3,4-Pentahydroxychalcone is used as an anti-inflammatory agent, potentially reducing inflammation and associated symptoms through its effects on immune response and cellular processes.
Used in Neurodegenerative Disease Treatment:
2',4',6',3,4-Pentahydroxychalcone shows promise in the treatment of neurodegenerative diseases, where it may act as a neuroprotective agent, potentially slowing down disease progression and improving the quality of life for affected individuals.
Used in Health and Wellness Industry:
Beyond direct medical applications, 2',4',6',3,4-Pentahydroxychalcone may also be incorporated into health and wellness products, such as dietary supplements and functional foods, to support overall health and well-being by leveraging its antioxidant properties.

Upstream product

• 139-85-5 3,4-dihydroxybenzaldehyde 
• 55260-28-1 1-[2,4,6-Tris-(tetrahydro-pyran-2-yloxy)-phenyl]-ethanone 
• 61854-89-5 3,4-di-[(tetrahydro-2H-pyran-2-yl)oxy]-benzaldehyde 
• 6515-06-6 3,4-bis-methoxymethoxy-benzaldehyde 
• 65490-09-7 2'-hydroxy-4',6'-bis(methoxymethoxy)acetophenone 
• 480-66-0 2,4,6-trihydroxyacetophenone 
• 314734-03-7 2'-hydroxy-3,4,4',6'-tetrakis(methoxymethoxy)chalcone 
• 54917-85-0 3,4-dibenzoyloxybenzaldehyde 

Downstream Products

• 491-70-3 2-(3,4-Dihydroxy-phenyl)-5,7-dihydroxy-chromen-4-on 
• 4049-38-1 eriodictyol 

Relevant academic research and scientific papers

Synthesis and Biological Evaluation of 2,4,6-Trihydroxychalcone Derivatives as Novel Protein Tyrosine Phosphatase 1B Inhibitors

A series of 2,4,6-trihydroxychalcone derivatives were synthesized and identified as reversible and competitive protein tyrosine phosphatase (PTP) 1B inhibitors with IC50 values in the micromolar range. Compound 4a had the greatest in vitro inhibition activity against PTP1B (IC50=0.27± 0.01μm) and the best selectivity (6.9-fold) for PTP1B relative to T-cell protein tyrosine phosphatases. The compounds identified herein provide a foundation on which to design specific inhibitors of PTP1B and other PTPs.

Natural and synthetic 2′-hydroxy-chalcones and aurones: Synthesis, characterization and evaluation of the antioxidant and soybean lipoxygenase inhibitory activity

A series of 2′-hydroxy-chalcones and their oxidative cyclization products, aurones, have been synthesized and tested for their antioxidant and lipoxygenase inhibitory activity. The natural product aureusidin (31) was synthesized in high yield by a new approach. An extensive structure-relationship study was performed and revealed that several chalcones and aurones possess an appealing pharmacological profile combining high antioxidant and lipid peroxidation activity with potent soybean LOX inhibition.

Synthesis and evaluation of 2′,4′,6′-trihydroxychalcones as a new class of tyrosinase inhibitors

In this study, we synthesized a series of hydroxychalcones and examined their tyrosinase inhibitory activity. The results showed that 2′,4′,6′-trihydroxychalcone (1), 2,2′,3,4′,6′-pentahydroxychalcone (4), 2′,3,4,4′,5,6′-hexahydroxychalcone (5), 2′,4′,6′-trihydroxy- 3,4-dimethoxychalcone (9) and 2,2′,4,4′,6′-pentahydroxychalcone (15) exhibited high inhibitory effects on tyrosinase with respect to l-tyrosine as a substrate. By the structure-activity relationship study, it was suggested that the 2′,4′,6′-trihydroxyl substructure in the chalcone skeleton were efficacious for the inhibition of tyrosinase activity. And also, the catechol structure on B-ring of chalcones was not advantageous for the inhibitory potency. Furthermore, 15 (IC50 = 1 μM) was found to show the highest activity out of a set of 15 hydroxychalcones, even better than both 2,2′,4,4′-tetrahydroxychalcone (13, IC50 = 5 μM) and kojic acid (16, IC50 = 12 μM), which were known as potent tyrosinase inhibitors. Kinetic study revealed that 15 acts as a competitive inhibitor of tyrosinase with Ki value of 3.1 μM.

DPPH radical scavenging reaction of hydroxy- and methoxychalcones

The DPPH radical scavenging activity of 2′,4′,6′- trihydroxy- and 2′-hydroxy-4′,6′-dimethoxychalcones carrying a 2,3- and 3,4-dihydroxylated, and 3,4,5-trihydroxylated B-ring was evaluated in alcoholic and non-alcoholic solvents. All test compounds scavenged more than two equivalent of radicals by a possible conversion to the corresponding B-ring quinones and in most cases subsequently underwent cyclization to aurones and flavanones, these being identified in the reaction solutions by an in situ NMR analysis. Interestingly, the reaction between 2′,3,4-trihydroxy-4′, 6′-dimethoxychalcone and the DPPH radical was significantly affected by the solvent used, which might be accounted for by the difference in readiness for cyclization to an aurone.

Synthesis and evaluation of antiplatelet activity of trihydroxychalcone derivatives

In an effort to develop potent antiplatelet agents, a series of trihydroxychalcones was synthesized and screened in vitro for their inhibitory effects on washed rabbit platelet aggregation induced by arachidonic acid (100 μM) and collagen (10 μg/ml). Of five compounds with potent inhibitory effects on arachidonic acid- and collagen-induced platelet aggregation, compound 4e was found to be the most potent. The structure-activity relationships suggested that antiplatelet activity was governed to a greater extent by the substituent on B ring of the chalcone template, and most of the active compounds had methoxy or dimethoxy groups on B ring.

3,4-Dihydroxychalcones as potent 5-lipoxygenase and cyclooxygenase inhibitors

A novel series of 3,4-dihydroxychalcones was synthesized to evaluate their effects against 5-lipoxygenase and cyclooxygenase. Almost all compounds exhibited potent inhibitory effects on 5-lipoxygenase with antioxidative effects, and some also inhibited cyclooxygenase. The 2',5'-disubstituted 3,4- dihydroxychalcones with hydroxy or alkoxy groups exhibited optimal inhibition of cyclooxygenase. We found that 2',5'-dimethoxy-3,4-dihydroxychalcone (37; HX-0836) inhibited cyclooxygenase to the same degree as flufenamic acid and 5-lipoxygenase, more than quercetin. Finally, these active inhibitors of 5- lipoxygenase inhibited arachidonic acid-induced mouse ear edema more than phenidone.

Anti-ulcer agent comprising chalcone derivative as effective ingredient and novel chalcone derivative

The present invention relates to an anti-ulcer agent comprising a compound represented by the following general formula I as the effective ingredient, and a novel chalcone derivative included in the compound represented by this general formula I: STR1 wherein X and Y independently stand for a hydrogen atom or together form a single bond, R1 stands for a hydroxyl group, an acetoxy group, a carboxymethoxy group or a methoxycarbonylmethoxy group, R2 stands for a hydrogen atom, an isoprenyl group, isopentyl group or a propyl group, R3 stands for hydroxyl group or a methoxy group, R4 stands for a hydrogen atom, a hydroxyl group or a methoxy group, R5 stands for a hydrogen atom, a hydroxyl group, a methoxy group or an isopentyl group, R6 stands for a hydroxyl group, a methoxy group or a carboxymethoxy group, and R7 stands for a hydrogen atom or a methoxy group.