Convenient synthesis of 5-aryl(alkyl)sulfanyl-1,10-phenanthrolines from 5,6-epoxy-5,6-dihydro-1,10-phenanthroline, and their activity towards fungal β-d-glycosidases

A broad series of novel 5-aryl(alkyl)sulfanyl-1,10-phenanthrolines has been prepared by a new simple procedure: a treatment of the commercially available 5,6-epoxy-5,6-dihydro-1,10-phenanthroline with various thiols in the presence of a base. Other functional groups attached to the thiol allow a use of the products as building blocks in synthesis of versatile ligands and in functionalization of surfaces. The synthesized phenanthrolines showed a moderate ability as activators or inhibitors of fungal β-d-glucosidases and β-d-galactosidases.