“Reazioni di ciclizzazione intramolecolare, deaminazione di sali di ammonio insaturi e studio delle proprietà biologiche dei prodotti ottenuti

The goal of this project is to synthesize novel dihydroisoindoline compounds by base-catalyzed intramolecular cyclization of ammonium salts containing 3-phenylprop-2-enyl group as a β,γ-unsaturated group, together with a 3-(4-methoxyphenyl)prop-2-ynyl group as a diene fragment. It is also planned to carry out aqueous-alkaline cleavage of the resulting dihydroisoindolinium salts in order to synthesize 2-(dialkylaminomethyl)-3-methyl- and 3-(dialkylaminomethyl)-2-methyl-1-phenyl-7-methoxynaphthalenes. At the same time, for the synthesis of terphenyls containing the target methoxy group, the Stevens rearrangement and deamination of 2,2-dialkyl(3-phenylprop-2-enyl)[3-(4-methoxyphenyl)prop-2-ynyl]ammonium bromides are planned.
The cyclization and rearrangement reactions carried out are of a general nature, theoretical significance, and also open up wide opportunities for the synthesis of new biologically active systems in an accessible way and with high yields. Physicochemical and molecular docking studies will be carried out, as well as a study of the biological properties of the synthesized new systems, considering their potential farmaceutical interest and biomedical application. In particular, will be tested antioxidant activity, cytotoxicity, proliferative/anti-proliferative effect, oxidative stress, anti-inflammatory properties. The rationale of the work plan (synthesis, chemical characterization, biological activity) will allow the screening of the products synthesized by the foreign countepart, focusing the attention on those with the most interesting biological properties, in order to develop new molecolar entity with potential biological interest.