25515-43-9

Usage

Uses

Used in Pharmaceutical Applications:
2',4'-dihydroxychalcone is used as a therapeutic agent for its potential to inhibit the growth of certain cancer cells, making it a candidate for cancer treatment. It is also being studied for its anti-diabetic properties, suggesting a role in managing blood sugar levels.
Used in Skincare and Cosmetic Products:
In the skincare and cosmetic industry, 2',4'-dihydroxychalcone is used as an antioxidant ingredient to protect the skin from oxidative stress and potentially slow down the aging process, capitalizing on its antioxidant benefits.
Used in Neurodegenerative Disease Research:
2',4'-dihydroxychalcone is used as a potential treatment in the research of neurodegenerative diseases, although further studies are required to understand its mechanisms of action and its applicability in human health.

Upstream product

• 102-92-1 cinnamoyl chloride 
• 108-46-3 recorcinol 
• 621-82-9 Cinnamic acid 
• 52923-29-2 1-(2-hydroxy-4-methoxyphenyl)-3-phenylprop-2-en-1-one 
• 140-10-3 (E)-3-phenylacrylic acid 
• 89-84-9 2',4'-dihydroxy-4-acetophenone 
• 100-52-7 benzaldehyde 
• 2079-52-9 1-(2,4-bis(allyloxy)phenyl)ethanone 
• 6515-05-5 2',4'-bis(methoxymethoxy)acetophenone 
• 6515-12-4 2',4'-Bis-methoxymethoxy-chalkon 
• 24532-21-6 1-[4-(benzyloxy)-2-hydroxyphenyl]-3-phenyl-2-propen-1-one 
• 895138-90-6 C₂₀H₂₀O₄ 
• 111841-07-7 2-hydroxy-4-(tetrahydropyran-2-yloxy)acetophenone 
• 22129-63-1 3-hydroxyphenyl cinnamate 

Downstream Products

• 93-58-3 benzoic acid methyl ester 
• 89-86-1 4-hydroxysalicylic acid 
• 65-85-0 benzoic acid 
• 6515-36-2 7-hydroxy-2-phenyl-chroman-4-one 
• 492-00-2 3,7-dihydroxyflavone 
• 6665-86-7 7-hydroxyflavone 
• 1453488-13-5 C₁₆H₁₆N₂O₂ 
• 51619-65-9 cordoin 

Relevant academic research and scientific papers

Chromone derivatives bearing pyridinium moiety as multi-target-directed ligands against Alzheimer's disease

A new serise of 7-hydroxy-chromone derivatives bearing pyridine moiety were synthesized, and evaluated as multifunctional agents against Alzheimer's disease (AD). Most of the compounds were good AChE inhibitors (IC50 = 9.8–0.71 μM) and showed remarkable BuChE inhibition activity (IC50 = 1.9–0.006 μM) compared with donepezil as the standard drug (IC50 = 0.023 and 3.4 μM). Compounds 14 and 10 showed the best inhibitory activity toward AChE (IC50 = 0.71 μM) and BuChE (IC50 = 0.006 μM), respectively. The ligand–protein docking simulations and kinetic studies revealed that compound 14 and 10 could bind effectively to the peripheral anionic binding site (PAS) of the AChE and BuChE through mixed-type inhibition. In addition, the most potent compounds showed acceptable neuroprotective activity on H2O2- and Aβ-induced.neurotoxicity in PC12 cells, more than standard drugs. The compounds could block effectively self- and AChE-induced Aβ aggregation. All the results suggest that compounds 14 and 10 could be considered as promising multi-target-directed ligands against AD.

Natural product-based design, synthesis and biological evaluation of 2′,3,4,4′-tetrahydrochalcone analogues as antivitiligo agents

A bioactive component, 2′,3,4,4′-tetrahydrochalcone (RY3-a) was first isolated from Vernohia anthelmintica (L.) willd seeds, and a set of its analogs, RY3-a-1–RY3-a-15 and RY3-c were designed and synthesized. Biological activity assays showed that RY3-c exhibited better melanogenesis and antioxidant activity and lower toxicity in comparison with RY3-a and butin. Further study tests showed that RY3-c exhibited better melanogenesis activity compared with the positive control 8-methoxypsoralan (8-MOP) in a vitiligo mouse model, suggesting that RY3-c is a good candidate antivitiligo agent. Mechanistic studies showed that RY3-c could repair cell damage induced by excessive oxidative stress and may exert melanin synthesis activity in the mouse melanoma B16F10 cell line by activating the mitogen-activated protein kinase (MAPK) pathway and the upregulation of c-kit.

Design, synthesis and QSAR study of 2′-hydroxy-4′-alkoxy chalcone derivatives that exert cytotoxic activity by the mitochondrial apoptotic pathway

Eleven 4′-alkoxy chalcones were synthesized and biologically evaluated for their antiproliferative activity against four human tumor cell lines (PC-3, MCF-7, HF-6, and CaSki). Compounds 3a-3d and 3f were selective against PC-3, with IC50 values ranging from 8.08 to 13.75 μM. In addition, chalcones 3a-3c did not affect the normal fibroblasts BJ cells. The most active and selective compounds were further evaluated for their effect on the progression of cell cycle in PC-3 cells, and chalcones 3a and 3c induced a G2/M phase arrest. Furthermore, it was found that these three chalcones induced the mitochondrial apoptotic pathway by regulating Bax and Bcl-2 transcripts and by increasing caspase 3/7 activation. Otherwise, the QSAR model indicates that the double bond of the α,β-unsaturated carbonyl, as well as the planar structure geometry, are important to the biological activity of the synthetized chalcones. Based on these studies, it was concluded that withdrawing substituents in ring A, decrease the antiproliferative activity. This is related to the possible mechanism of action of these compounds, where a Michael addition needs to take place in order to be a potent anticancer agent.

Design, synthesis, biological activity and structure-activity relationship studies of chalcone derivatives as potential anti-Candida agents

Vulvovaginal candidiasis (VVC) affects millions of women around the world every year. Candida albicans is the most frequently isolated pathogen in women and its rapid ability to develop resistance to first and second line therapies has boosted the search

Design, synthesis and bioactivity of chalcones and its analogues

The Vernohia anthelmintica L.'s extract is one of the most popular Uygur medicines used for vitiligo. It is believed that the chalcone compounds of the plant play an important role in the treatment since they may activate tyrosinase and improve melanin production. In this study, twenty-one chalcones and nine analogues were synthesized in view of three different components of chalcone (A, B ring and α, β-unsaturated carbonyl). After biological evaluation of their activity on tyrosinase in cell-free systems, the result showed that most compounds (except polyhydroxy chalcones) possess activator effect on the tyrosinase, especially for 13a–15a, 20a and 1b, which bearing a comparable activity to the positive control 8-MOP. SAR of these tyrosinase activator was summed up for the first time as well. Finally, compound 13a was found to increase melanin contents and tyrosinase activity 1.75 and 1.3 fold, respectively, compared with that of untreated murine B16 cells at the concentration of 40?μg/mL.

Synthesis, antitubercular activity, and molecular modeling studies of analogues of isoliquiritigenin and liquiritigenin, bioactive components from Glycyrrhiza glabra

Isoliquiritigenin (ISL, 1) and liquiritigenin (LTG, 2) were isolated from the rhizomes of Glycyrrhiza glabra. In an attempt to develop potent and selective antituberculosis agents, a series of ISL analogues were synthesized mainly via acid- and base-catalyzed Claisen-Schmidt condensation reaction for their antitubercular activity. Compared to ISL (MIC = 25 μg/mL), analogues 5, 8, and 10 showed similar antitubercular activity, but, interestingly, 6, 7, and 15 exhibited twofold higher activity (MIC = 12.5 μg/mL) over ISL, against Mycobacterium tuberculosis. Among the LTG derivatives, LTG 4′-acetate and LTG-oxime were found to be as active (MIC = 25 μg/mL) as LTG. It is the first report on antimycobacterial activity of these ISL- and LTG-based derivatives. Molecular docking and in silico ADME studies revealed that compounds 6, 7, and 15 are potent inhibitors of M. tuberculosis H37Rv alanine dehydrogenase and showed compliance with standard parameters of drug likeness.

Cytotoxic activity of substituted chalcones in terms of molecular electronic properties

Global chemical reactivity descriptors and lipophilicity (log P) were evaluated via density functional theory in order to clarify the structure-cytotoxic activity relationships of substituted chalcones. Stepwise multiple regression was employed to establish correlation between descriptors and cytotoxic activity against three cancer cell lines (HL-60, NALM-6 and WM-115) for 11 compounds. Regression analysis revealed that electrophilicity index and chemical potential significantly contributed in explaining of chalcones cytotoxic potential. Moreover, the established structure-activity relationships based on electronic structure properties allow indicating the substructures responsible for their cytotoxic activity. The study has also been supported by crystallographic data of 2-chloro-2′-hydroxychalcone.

Quantum-chemical analysis of the Algar-Flynn-Oyamada reaction mechanism

This work is devoted to improving the understanding of Algar-Flynn-Oyamada reaction mechanism and the analysis of factors that affect the formation of flavonols. The calculation of thermodynamic parameters for the key reaction steps pointed to a mechanism involving chalcone epoxides as intermediates. A correlation was identified between the nucleophilicity of oxygen atom at position 2' of epoxide anions and the yields of flavonols. An increased charge at the nucleophilic center was shown to reduce the effectiveness of β-cyclization of epoxide anions.

Synthesis of butein analogues and their anti-proliferative activity against gefitinib-resistant non-small cell lung cancer (NSCLC) through Hsp90 inhibition

Non-small cell lung cancer (NSCLC) is the most common type of lung cancer representing 85% of lung cancer patients. Despite several EGFR-targeted drugs have been developed in the treatment of NSCLC, the clinical efficacy of these EGFR-targeted therapies i

Calcium hydroxide is an efficient catalyst for synthesis of polyhydroxy chalcones

Calcium hydroxide was found to be an efficient catalyst for synthesis of polyhydroxy chalcones. This method has been employed to synthesize various 2′,4′-dihydroxychalcones having various substituents on the B ring. The merits of this method include shorter reaction time, inexpensive and easily available catalyst, high yield, and easy workup compared to other reported methods. Copyright Taylor and Francis Group, LLC.