Damiano Tanini

The antimicrobial properties of one of the most important secondary metabolites, Eugenol (EU), inspired us to design and synthesize three different series of derivatives enhancing its parent compound’s anti-Helicobacter pylori activity. Thus, we prepared semisynthetic derivatives through (A) diazo aryl functionalization, (B) derivatization of the hydroxy group of EU, and (C) elongation of the allyl radical by incorporating a chalcogen atom. The antibacterial evaluation was performed on the reference NCTC 11637 strain and on three drug-resistant clinical isolates and the minimal inhibitory and bactericidal concentrations (MICs and MBCs) highlight the role of chalcogens in enhancing the antimicrobial activity (less than 4 µg/mL for some compounds) of the EU scaffold (32–64 µg/mL).

A scalable and operationally simple on water seleno‐mediated reduction of nitroarenes to the respective aryl amines with NaBH 4 is described. The reaction proceeds under transition metal‐free conditions and is promoted by the formation of Na 2 Se, which is the effective reducing agent involved in the mechanism. This mechanistic information enabled the development of a mild NaBH 4 ‐free protocol for the selective reduction of nitro derivatives bearing labile moieties, including nitrocarbonyl compounds. The selenium‐containing aqueous phase can be successfully reused up to four reduction cycles, thus further improving the efficiency of the protocol disclosed.