108979-08-4

Usage

Uses

Used in Organic Synthesis:
2-Propen-1-one, 3-(4-bromophenyl)-1-(2-hydroxy-4,6-dimethoxyphenyl)is used as a building block in organic synthesis for the creation of various chemical compounds.
Used in Flavoring Agents:
2-Propen-1-one, 3-(4-bromophenyl)-1-(2-hydroxy-4,6-dimethoxyphenyl)is used as a flavoring agent in the food industry to impart unique flavors to food products.
Used in Medicinal and Pharmaceutical Applications:
2-Propen-1-one, 3-(4-bromophenyl)-1-(2-hydroxy-4,6-dimethoxyphenyl)is used as a potential candidate for medicinal and pharmaceutical applications due to the presence of bromine and hydroxyl groups in its structure.
Used in Health and Skincare Products:
2-Propen-1-one, 3-(4-bromophenyl)-1-(2-hydroxy-4,6-dimethoxyphenyl)is used in health and skincare products due to its antioxidant properties provided by the dimethoxy substituents.

Upstream product

• 108-73-6 3,5-dihydroxyphenol 
• 480-66-0 2,4,6-trihydroxyacetophenone 
• 871878-99-8 1-(2,4-dimethoxyphenyl)-2-hydroxyethanone 
• 1122-91-4 4-bromo-benzaldehyde 
• 90-24-4 2-hydroxy-4,6-dimethoxyacetophenone 
• 99-90-1 para-bromoacetophenone 

Downstream Products

• 350982-89-7 (Z)-2-(4-bromobenzylidene)-4,6-dimethoxybenzofuran-3(2H)-one 
• 1394173-49-9 C₁₇H₁₄Br₂O₄ 
• 3791-76-2 2’-hydroxy-4’,6’-dimethoxydihydrochalcone 

Relevant academic research and scientific papers

Targeting the MDM2-p53 protein-protein interaction with prenylchalcones: Synthesis of a small library and evaluation of potential antitumor activity

Prenylation of several bioactive scaffolds is a very interesting strategy used in Medicinal Chemistry in order to improve biological/pharmacological effects. A small library of prenylchalcones was synthesized and evaluated for the ability to inhibit the MDM2-p53 interaction using a yeast-based assay. The capacity of all synthesized prenylchalcones and their non-prenylated precursors to inhibit the growth of human colon tumor HCT116 cells was also evaluated. The obtained results led to the identification of a hit compound, prenylchalcone 2e, which behaved as potential inhibitor of the MDM2-p53 interaction in yeast, and showed improved cytotoxicity against human tumor cells expressing wild-type p53, including liver hepatocellular carcinoma HepG2, breast adenocarcinoma MCF-7, and malignant melanoma A375 cells. In colon cancer cells, it was also shown that the growth inhibitory effect of prenylchalcone 2e was associated with the induction of cell cycle arrest, apoptosis, and increased protein expression levels of p53 transcriptional targets. Moreover, computational docking studies were performed in order to predict docking poses and residues involved in the MDM2-p53 potential interaction.

Antischistosomal properties of aurone derivatives against juvenile and adult worms of Schistosoma mansoni

Schistosomiasis is a neglected disease caused by helminth flatworms of the genus Schistosoma, affecting over 240 million people in more than 70 countries. The treatment relies on a single drug, praziquantel, making urgent the discovery of new compounds. A

Development of a novel nitric oxide (NO) production inhibitor with potential therapeutic effect on chronic inflammation

Inflammation is a complex biological response to stimuli. Activated macrophages induced excessively release of pro-inflammatory cytokines and mediators such as endogenous radical nitric oxide (NO) play a significant role in the progression of multiple inflammatory diseases. Both natural and synthetic chalcones possess a wide range of bioactivities. In this work, thirty-nine chalcones and three related compounds, including several novel ones, based on bioactive kava chalcones were designed, synthesized and their inhibitory effects on NO production in RAW 264.7 cells were evaluated. The novel compound (E)-1-(2′-hydroxy-4′,6′-dimethoxyphenyl)-3-(3-methoxy-4-(3-morpholinopropoxy)phenyl)prop-2-en-1-one (53) exhibited a better inhibitory activity (84.0%) on NO production at 10 μM (IC50 = 6.4 μM) with the lowest cytotoxicity (IC50 > 80 μM) among the tested compounds. Besides, western blot analysis indicated that compound 53 was a potent down-regulator of inducible nitric oxide synthase (iNOS) protein. Docking study revealed that compound 53 also can dock into the active site of iNOS. Furthermore, at the dose of 10 mg/kg/day, compound 53 could both significantly suppress the progression of inflammation on collagen-induced arthritis (CIA) and adjuvant-induced arthritis (AIA) models. In addition, the structure-activity relationship (SAR) of the kava chalcones based analogs was also depicted.

Design, synthesis and docking studies of flavokawain B type chalcones and their cytotoxic effects on MCF-7 and MDA-MB-231 cell lines

Flavokawain B (1) is a natural chalcone extracted from the roots of Piper methysticum, and has been proven to be a potential cytotoxic compound. Using the partial structure of flavokawain B (FKB), about 23 analogs have been synthesized. Among them, compounds 8, 13 and 23 were found in new FKB derivatives. All compounds were evaluated for their cytotoxic properties against two breast cancer cell lines, MCF-7 and MDA-MB-231, thus establishing the structure-activity relationship. The FKB derivatives 16 (IC50 = 6.50 ± 0.40 and 4.12 ± 0.20 μg/mL), 15 (IC50 = 5.50 ± 0.35 and 6.50 ± 1.40 μg/mL) and 13 (IC50 = 7.12 ± 0.80 and 4.04 ± 0.30 μg/mL) exhibited potential cytotoxic effects on the MCF-7 and MDA-MB-231 cell lines. However, the methoxy group substituted in position three and four in compound 2 (IC50 = 8.90 ± 0.60 and 6.80 ± 0.35 μg/mL) and 22 (IC50 = 8.80 ± 0.35 and 14.16 ± 1.10 μg/mL) exhibited good cytotoxicity. The lead compound FKB (1) showed potential cytotoxicity (IC50 = 7.70 ± 0.30 and 5.90 ± 0.30 μg/mL) against two proposed breast cancer cell lines. It is evident that the FKB skeleton is unique for anticancer agents, additionally, the presence of halogens (Cl and F) in position 2 and 3 also improved the cytotoxicity in FKB series. These findings could help to improve the future drug discovery process to treat breast cancer. A molecular dynamics study of active compounds revealed stable interactions within the active site of Janus kinase. The structures of all compounds were determined by 1H-NMR, EI-MS, IR and UV and X-ray crystallographic spectroscopy techniques.

In Vitro and in Vivo Antischistosomal Activities of Chalcones

In this study, we evaluated the in vitro and in vivo schistosomicidal activities of chalcones against Schistosoma mansoni worms. In vitro assays revealed that chalcones 1 and 3 were the most active compounds, without affecting significantly mammalian cells. Confocal laser scanning microscopy and scanning electron microscopy studies revealed reduction on the numbers of tubercles and morphological alterations in the tegument of S. mansoni worms after in vitro incubation with chalcones 1 and 3. In a mouse model of schistosomiasis, the oral treatment (400 mg/kg) with chalcone 1 or 3 significantly caused a total worm burden reduction in mice. Chalcone 1 showed significant inhibition of the S. mansoni ATP diphosphohydrolase activity, which was corroborated by molecular docking studies. The results suggested that chalcones could be explored as lead compounds with antischistosomal properties.

Mechanisms of action and structure-activity relationships of cytotoxic flavokawain derivatives

22 Flavokawain derivatives (FKd) were obtained by one step syntheses in order to conduct a SAR study to understand the structural requirements for optimum and selective cytotoxicity. FKd and natural flavokawains A and B found into kava, a South Pacific traditional beverage, were evaluated against nine cancer and one healthy cell lines. The targeted cell cycle phases as well as the effects on the induction of apoptosis and cell cycle protein levels were investigated. Therapeutic improvements (more activity and selectivity) were achieved with FKd compared to natural flavokawains and notably with the 2′,3,4′,6′-tetramethoxychalcone (FKd 19). FKd induced a G1/S arrest on p53 wild-type cells and an M arrest on p53 mutant-type, via the up-regulation of p21 and cyclin B1 proteins, followed by apoptosis. Moreover, FKd exhibited a 24?h-effect on Akt/mTor normal cells versus a 48?h-effect on Akt/mTor up-regulated cells. The SAR study resulted in the conclusion that trimethoxy A-ring allowed the best compromise between cytotoxicity and selectivity, as well as the substitution of the meta position on the B-ring and the use of halogens substituents.

Synthesis of chalcone analogues with increased antileishmanial activity

Eighteen analogues of an active natural chalcone were synthesized using xanthoxyline and some derivatives, and these analogues were tested for selective activity against both promastigotes and intracellular amastigotes of Leishmania amazonensis in vitro. Three analogues (10, 12, and 19) containing nitro, fluorine or bromine groups, respectively, displayed increased selective activity against the parasites as compared with the natural chalcone. The nitrosylated chalcone 10 was also tested intralesionally in infected mice and was found to be as effective as Pentostan reference drug at a dose 100 times higher than that of the chalcone in controlling both the lesion growth and the parasite burden.

Antifungal activity and studies on mode of action of novel xanthoxyline-derived chalcones

Chalcones and chalcone-like compounds, most of them new ones, prepared by base-catalyzed condensation of appropriate aldehydes and xanthoxyline, were tested for antifungal properties against a panel of yeasts, hialohyphomycetes as well as dermatophytes with the agar dilution assay. Results indicate that neither the sole presence of a xanthoxyline-like substitution pattern nor a 2′-OH substituent on ring A are sufficient for these compounds to have antifungal properties. The chalcone 3-(2-chlorophenyl)-1- (2′-hydroxy-4′,6′-dimethoxyphenyl)prop-2-en-1-one, with a Cl atom in the ortho position of benzene ring B showed the best antifungal activity against standardized strains of Trichophyton rubrum (MIC = 12.5 μg/mL) and inhibited all of the ten clinical isolates of T. rubrum tested (MIC at which 50% [MIC50] and 90% [MIC90] of the isolates were inhibited = 12.5 and 25 μg/mL). Regarding its mode of action, the Neurospora crassa assay showed a blotchy appearance in the inhibition halo produced by this chalcone, strongly suggesting that it could act by inhibiting the fungal cell wall. This chalcone seems to be an hyphal malformation inducer, since a clear curling of the hypha was observed in this hazy zone at a magnification of X 400. This work strongly contributes to the knowledge of the antifungal properties of hydroxy-chalcones.