Synthesis and biological activity of nitrogen-containing derivatives of estafiatin

Abstract

The reactions of guaianolide of estafiatin with various amines were investigated. It was shown that the aminolysis reactions of γ-lactone ring of estafiatin or reactions of Michael-type conjugate addition or tandem conversions of Michael and Knoevenagel-type were carried out depending on the nature of amines. The regularity of proceeding of estafiatin reactions with secondary aliphatic and aliphatic-aromatic amines was detected. It lies in the fact that the reactions proceed exclusively by Michael reaction and they are completely regioand stereoselective. It was revealed that synthetic nitrogen-containing derivatives of estafiatin had antibacterial and antioxidant activity.