SYNTHESIS AND ANTITUMOR ACTIVITY OF SPERGUALIN ANALOGUES

II. CHEMICAL MODIFICATION OF THE SPERMIDINE MOIETY

Abstract

Chemical modifications of the spermidine moiety of an antitumor antibiotic, spergualin (Ia), and the structure-activity relationship are described. Replacement of spermidine with other poly amines decreased the antitumor activity against mouse leukemia LI 210. Analogues containing an oxidized spermidine moiety that probably formed during oxidation with amine oxidase were inactive. Spermidine is indispensable for the antitumor activity. A facile method for the synthesis of glyoxyloyl polyamine, a key intermediate of spergualin-related compounds, is also reported.