Synthesis and antioxidant activity of 1-R-3-(2-fluorophenyl)selenoureas containing polycyclic fragments

We have developed an improved two-stage approach to the synthesis of 2-fluorophenylisoselenocyanate from 2-fluoroaniline, which at the first stage uses a mixture of solvents, dichloromethane and tert-butanol, allowing us to significantly simplify the isolation and purification of the target product. The reaction of 2-fluorophenylisoselenocyanate with adamantyl-containing and bicyclic amines gave 1,3-disubstituted selenoureas in 27-83% yields. The obtained selenoureas were studied for their antioxidant properties and antiradical activity. A number of compounds demonstrated the antioxidant properties several times exceeding the values of the reference Trolox and Ionol.

Automated summary

We have developed an improved synthesis method that simplifies the isolation and purification steps of the target compound. The synthesized compounds exhibit excellent antioxidant properties and antiradical activity.