38239-54-2

Upstream product

• 2960-55-6 (E)-3-(4-nitrophenyl)-1-phenylprop-2-en-1-one 
• 98-86-2 acetophenone 
• 555-16-8 4-nitrobenzaldehdye 
• 1222-98-6 4-nitrochalcone 

Downstream Products

• 72758-78-2 cis-1-(4-aminophenyl)-3-phenyl-1-propen-3-one 
• 1151741-43-3 2-bromo-N-(4-((E)-3-oxo-3-phenylprop-1-enyl)phenyl)acrylamide 

Relevant academic research and scientific papers

Applying the designed multiple ligands approach to inhibit dihydrofolate reductase and thioredoxin reductase for anti-proliferative activity

The development of multi-targeting drugs is currently being explored as an attractive alternative to combination therapy, especially for the treatment of complex diseases such as cancer. Dihydrofolate reductase (DHFR) and thioredoxin reductase (TrxR) are enzymes belonging to two unrelated cellular pathways that are known to contribute towards cancer cell growth and survival. In order to evaluate whether simultaneous inhibition of DHFR and TrxR by dihydrotriazines (DHFR-targeting) and chalcones (TrxR-targeting) may be beneficial, breast MCF-7 and colorectal HCT116 carcinoma cells were treated with combinations of selected dihydrotriazines and chalcones at a 1:1 M ratio. Two combinations demonstrated synergy at low-to-moderate concentrations. Based on this result, four merged dihydrotriazine-chalcone compounds were designed and synthesized. Two compounds, 11a [DHFR IC50 = 56.4 μM, TrxR IC50 (60 min) = 12.6 μM] and 11b [DHFR IC50 = 2.4 μM, TrxR IC50 (60 min) = 10.1 μM], demonstrated in vitro inhibition of DHFR and TrxR. The compounds showed growth inhibitory activity against MCF-7 and HCT116 cells, but lacked cytotoxicity. Molecular docking experiments showed 11b to possess rational binding modes to both the enzymes. In conclusion, this study has not only identified the dihydrotriazine and chalcone scaffolds as good starting points for the development of dual inhibitors of DHFR and TrxR, but also demonstrated the synthetic feasibility of producing a chemical entity that could result in simultaneous inhibition of DHFR and TrxR. Future efforts to improve the antiproliferative profiles of such compounds will look at alternative ways of integrating the two pharmacophoric scaffolds.

Hybrid α-bromoacryloylamido chalcones. Design, synthesis and biological evaluation

Research into the anti-tumor properties of chalcones has received significant attention over the last few years Two novel large series of α-bromoacryloylamido chalcones 1a-m and 2a-k containing a pair of Michael acceptors in their structures, corresponding to the α-bromoacryloyl moiety and the α,β-unsaturated ketone system of the chalcone framework, were synthesized and evaluated for antiproliferative activity against five cancer cell lines. Such hybrid derivatives demonstrated significantly increased anti-tumor activity compared with the corresponding amino chalcones. The most promising lead molecules were 1k, 1m and 2j, which had the highest activity toward the five cell lines. Flow cytometry with K562 cells showed that the most active compounds resulted in a large proportion of the cells entering in the apoptotic sub-G0-G1 peak. Moreover, compound 1k induced apoptosis through the mitochondrial pathway and activated caspase-3.

Pd-C/ammonium formate: A selective catalyst for the hydrogenation of chalcones to dihydrochalcones

Pd-C/ammonium formate is a highly efficient catalyst for the selective hydrogenation of chalcones to dihydrochalcones (DHCs). The reaction proceeds under mild conditions and the Pd-C catalyst is recovered without loss of activity.

Spectral properties and photochemical activity of chalcone derivatives

A relationship is found between spectral-luminescent and photochemical properties for mono-and disubstituted chalcone derivatives R1CO-CH=CHR2 [R1, R2 = Ph, 4-FC6H4, 4-BrC6H4, 2-furyl, 2-thienyl, 4-(PhCONH)C6H4, 4-NH2C6H4, 4-Me2NC6H4].