Summary:
Enones are a group of compounds with a variety of biological effects. Some of
them showed: anti-inflammatory, scavenging of free radicals, anticancer,
antitumor, lavrae, antioxidant activity and inhibition of lipid peroxidation.
We reviewed the literature data on chalcones and aurones and with the help of
the C-QSAR program extracted quantitative structure-activity relationships.
Using these conclusions we proceeded with the synthesis of a series of
compounds bearing the enone structure as, chalcones, aurones and 4’’-4’’’
-trimethyleno-dioxy-bis substituted chalcones. Synthesis of chalcones and 4’’
-4’’’-trimethyleno-dioxy-bis substituted chalcones is based on the
Claisen-Schmidt condensation and the synthesis of aurones follows an oxidative
cyclization between mercury acetate and a 2’-hydroxy-chalcone. The compounds
were studied both in vitro and in vivo .
Pharmacochemical tests in vitro:
DPPH (2,2-diphenyl-1-picrylhydrazyl) radical scanvenging assay
Inhibition of lipid peroxidation using AAPH [2,2’
-azobis-2-methyl-propanimidamide]
Soybean lipoxygenase inhibition assay
Interact ion with glutathione
Biological experiments in vivo
Inhibition of the carrageenin-induced rat edema (CPE)
Toxicity against mosquito larvae.
Efforts are conducted a) to correlate quantitatively the in vitro / in vivo
results with the most important physicochemical properties of the molecules and
b) to clarify the correlation of actions among them in order to propose a
possible mechanism of action.
Keywords:
Enone group, Chalcones, Aurones, Inflammation, Cancer