63529-05-5

Upstream product

• 24672-82-0 1-[2,4-dihydroxy-3,5-bis-(3-methyl-but-2-enyl)-phenyl]-ethanone 
• 123-08-0 4-hydroxy-benzaldehyde 
• 89-84-9 2',4'-dihydroxy-4-acetophenone 
• 870-63-3 prenyl bromide 
• 40663-68-1 4-(2-propenyloxy)benzaldehyde 
• 115-18-4 2-methyl-3-buten-2-ol 
• 1314539-32-6 (E)-1-(2-hydroxy-4-(methoxymethoxy)-3,5-bis(3-methylbut-2-en-1-yl)phenyl)-3-(4-(methoxymethoxy)phenyl)prop-2-en-1-one 
• 1544322-35-1 1-(5-iodo-2,4-bis(methoxymethoxy)phenyl)ethanone 
• 6515-05-5 2',4'-bis(methoxymethoxy)acetophenone 
• 1544322-28-2 (E)-1-(5-iodo-2,4-bis(methoxymethoxy)phenyl)-3-(4 (methoxymethoxy)phenyl)prop-2-en-1-one 
• 952647-84-6 (E)-1-(2-hydroxy-4-(methoxymethoxy)-5-(3-methylbut-2-en-1-yl)phenyl)-3-(4-(methoxymethoxy)phenyl)prop-2-en-1-one 

Downstream Products

• 99-96-7 4-hydroxy-benzoic acid 

Relevant academic research and scientific papers

Synthetic methods for prenylated chalcones and pyranochalcones

The inventors of the present invention invented a simple and effective way to synthesize compounds 1-9 of natural prenylated chalcones and pyrano chalcones by using Claisen-Schmidt condensation as a main step. In addition, an anti-inflammatory effect of synthetic compounds was evaluated in RAW 264.7 macrophages which were stimulated with a lipopolysaccharide. As a result, chalcone compounds having prenyl groups in a ring A (an acetophenone part) show weak inhibition or no inhibition on the generation of nitrogen oxide while chalcones (5, 6, 8, and 9) having no prenyl groups in the ring A show normal or good activity, and have no cytotoxicity.COPYRIGHT KIPO 2017

Synthesis and pharmacological properties of naturally occurring prenylated and pyranochalcones as potent anti-inflammatory agents

An efficient approach has been developed for the synthesis of naturally occurring prenylated chalcones viz. kanzonol C (1), stipulin (2), crotaorixin (3), medicagenin (4), licoagrochalcone A (5) and abyssinone D (6) along with the pyranochalcones paratocarpin C (7), anthyllisone (8) and 3-O-methylabyssinone A (9). The key step of the synthesis is a Claisen-Schmidt condensation. Subsequently, their anti-inflammatory effects were investigated in lipopolysaccharides (LPSs)-induced RAW-264.7 macrophages. Of the synthesized chalcones, compounds 5 (IC50 = 10.41 μmol/L), 6 (IC50 = 9.65 μmol/L) and 8 (IC50 = 15.34 μmol/L) show remarkable activity with no cytotoxicity. Compound 9 (IC50 = 4.5 μmol/L) exhibits maximum (83.6%) nitric oxide (NO) inhibition, but shows slight cytotoxicity. The results reveal that the chalcones bearing the prenyl group at 3- and/or 5-position on ring A (acetophenone moiety), i.e., 1-4 and 7 show weak, or no inhibition activity, whereas chalcones having the prenyl group only on ring B (aldehyde part), i.e., 5, 6 and 8 show significant activity on the production of inflammatory mediated NO with no cytotoxicity.

Synthesis and anti-cancer activity evaluation of novel prenylated and geranylated chalcone natural products and their analogs

Four natural chalcones bearing prenyl or geranyl groups, i.e., bavachalcone (1a), xanthoangelol (1b), isobavachalcone (1c), and isoxanthoangelol (1d) were synthesized by using a regio-selective iodination and the Suzuki coupling reaction as key steps. The first total synthesis of isoxanthoangelol (1d) was achieved in 36% overall yield. A series of diprenylated and digeranylated chalcone analogs were also synthesized by alkylation, regio-selective iodination, aldol condensation, Suzuki coupling and [1,3]-sigmatropic rearrangement. The structures of the 11 new derivatives were confirmed by 1H NMR, 13C NMR and HRMS. The anticancer activity of these new chalcone derivatives against human tumor cell line K562 were evaluated by MTT assay in vitro. SAR studies suggested that the 50-prenylation/geranylation of the chalcones significantly enhance their cytotoxic activity. Among them, Bavachalcone (1a) displayed the most potent cytotoxic activity against K562 with IC50 value of 2.7 mM. The morphology changes and annexin-V/PI staining studies suggested that those chalcone derivatives inhibited the proliferation of K562 cells by inducing apoptosis.

A PRENYLATED CHALCONE FROM CROTALARIA MEDICAGINEA

Key Word Index-Crotalaria medicaginea; Leguminosae; roots; 3',5'-di-isopentenyl; 2',4',4-trihydroxy chalcone. A new prenylated chalcone has been characterized from the root of Crotalaria madicaginea.