1258290-39-9Relevant academic research and scientific papers
Synthetic methods for prenylated chalcones and pyranochalcones
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Paragraph 0042; 0059; 0060, (2017/04/27)
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
Damodar, Kongara,Kim, Jin-Kyung,Jun, Jong-Gab
, p. 698 - 702 (2016/05/19)
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.
