104236-79-5

Upstream product

• 621-59-0 isovanillin 
• 89-84-9 2',4'-dihydroxy-4-acetophenone 
• 121-33-5 vanillin 
• 5460-32-2 1-iodo-3,4-dimethoxybenzene 
• 67756-04-1 1-(2,4-dimethoxy-phenyl)-prop-2-en-1-one 
• 100753-43-3 (E)-1-(2,4-dimethoxyphenyl)-3-(3,4-dimethoxyphenyl)prop-2-en-1-one 

Downstream Products

• 50297-25-1 2,3'-dihydroxy-4-(carbethoxymethoxy)-4'-methoxychalcone 
• 66281-59-2 2,3-dihydroxy-4-(carboxymethoxy)-4'-methoxychalcone 
• 2150-11-0 3',4',7-trihydroxyflavone 
• 54867-60-6 7-hydroxy-2-(3-hydroxy-4-methoxyphenyl)-benzo(b)pyran-4-one 
• 76426-28-3 7-hydroxy-2-(3-hydroxy-4-methoxyphenyl)chroman-4-one 

Relevant academic research and scientific papers

Differential effects of synthesized 2′-oxygenated chalcone derivatives: Modulation of human cell cycle phase distribution

Ten structurally related 2′-oxygenated chalcone derivatives, bearing either hydroxy and/or methoxy substituents on the A and B rings, were synthesized through Claisen-Schmidt condensation. The synthesis procedure was relatively easy and had an acceptable yield. The in vitro cytotoxicities of these compounds against the human tumor cells such as Jurkat, U937 cells, and normal cells PHA stimulated PBMCs were investigated. Among those, compounds 1 (IC50=2.5μM), 2 (1.7μM), and 8 (3.2μM) showed potent inhibitory activity toward Jurkat cell line. In parallel, compounds 1 (6.7μM), 2 (1.5μM), and 10 (5.3μM) showed the highest activity against U937 cell line. However, the chalcones also inhibit the PHA stimulated PBMCs cells, but the IC50 values were relatively high when compared to the tumor cell line values. Studies were also on the effect of synthesized chalcones on the cell cycle phase distribution. In Jurkat cell line, compounds 7 and 9 showed the highest activity and the most striking effect in reduction of the percentage of cells in the S phase, which was associated with an increase of cells in G2/M phase. In U937 cell line, compound 3 increased the proportion of cells in the G0/G1 phase and reduced the proportion in S phase. In contrast, compounds 1, 9, and 10 showed a decrease effect on the percentage of cells in S phase and an increase effect on the percentage of cells in the G2/M phase of the cell cycle. Whereas in the case of PHA stimulated PBMCs, compounds 1, 4, 8, and 10 increased the percentage of cells in G2/M phase, which was associated with a decrease effect in the S phase of the cell cycle.

Discovery of isoliquiritigenin analogues that reverse acute hepatitis by inhibiting macrophage polarization

Screening a natural product library of 850 compounds yield isoliquiritigenin as an effective anti-inflammatory agent by inhibiting the production of pro-inflammatory NO induced by Pam3CSK4, while its activity accompanied by toxicity. Further studies obtained the optimized isoliquiritigenin derivative SMU-B14, which can inhibit Pam3CSK4 triggered toll-like receptor 2 (TLR2) signaling with low toxicity and high potency. Preliminary mechanism studies indicated that SMU-B14 worked through TLR2/MyD88, phosphorylation of IKKα/β, leading to the reduce degradation of NF-κB related IKBα and p65 complex, then inhibited the production of inflammatory cytokines, such as TNF-α, IL-6, IL-1β both in human and murine cell lines. Subsequent polarization experiments showed SMU-B14 significant reversed the polarization of M1 phenotype primary macrophage activated by Pam3CSK4 in vitro, and reduced the infiltration of neutrophil and polarization of M1-type macrophage, decreased serum alanine transaminase (ALT), as a result protected liver from being injured in vivo. In summary, we obtained an optimized lead compound SMU-B14 and found it functionally blocked TLR2/MyD88/NF-κB signaling pathway to down-regulate the production of inflammatory cytokines resulted significant liver protection property.

Synthesis and evaluation of butein derivatives for in vitro and in vivo inflammatory response suppression in lymphedema

Herein, we demonstrate that butein (1) can prevent swelling in a murine lymphedema model by suppressing tumor necrosis factor α (TNF-α) production. Butein derivatives were synthesized and evaluated to identify compounds with in vitro anti-inflammatory activity. Among them, 20 μM of compounds 7j, 7m, and 14a showed 50percent suppression of TNF-α production in mouse peritoneal macrophages after lipopolysaccharide stimulation. Compound 14a, exhibited the strongest potency with an in vitro IC50 of 14.6 μM and suppressed limb volume by 70percent in a murine lymphedema model. The prodrug strategy enabled a six-fold increase in kinetic solubility of compound 1 and five-fold higher levels of active metabolite in the blood for compound 14a via oral administration in the pharmacokinetics study. We suggest that the compound 14a could be developed as a potential therapeutic agent targeting anti-inflammatory activity to alleviate lymphedema progression.

Preparation method of chalcone, dihydrochlcone and flavone compound and application

The invention discloses a preparation method of chalcone, dihydrochlcone and flavone compound and an application. The preparation method and application disclosed by the invention have the beneficialeffects that 3,4',6'-trihydroxy-4-methoxychalcone has stronger inhibiting effect to a-glucosidase and can be used for reducing postprandial hyperglycemia; 4-dimethylaminochalcone, 4-hydroxychalcone, 3-hydroxy-4-methoxychalcone and 3,4',6'-trihydroxy-4-methoxychalcone have more obvious inhibiting effect to nonenzymatic glycation and can be used for treating diabetes and atherosclerosis.

Cytotoxic and antimicrobial activities of some synthetic flavones

Several flavones have been synthesized and their biocidal activity investigated along with their corresponding chalcones against some bacterial and fungal strains as well as brine shrimp nauplii. Compounds 13 and 14 show good antibacterial, antifungal and

The heck coupling reaction using aryl vinyl ketones: Synthesis of flavonoids

In our previous communication, an α,β-unsaturated aryl ketone was employed as the substrate olefin, which underwent arylation in the Heck coupling reaction. The use of this reagent has allowed us to design a new strategy for the synthesis of flavonoids. In this paper, we illustrate the versatility of the procedure, which was used for the preparation of several chalcones. According to our synthetic scheme, several aryl iodides, selected in order to obtain chalcones differently substituted in ring B, were treated with α,β-unsaturated ketones. All reported syntheses gave high yields. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004.