Studies on antiviral agents. III. Synthesis and in vitro antiviral activity of 1-N-higher-acyl-3"-N-functionalized acylkanamycin A derivatives.

The synthesis and antiviral activity of 1-N-palmitoyl- or 1-N-(3-hydroxytetradecanoyl)-kanamycin A derivatives (7,8) having various type of acyl substituents at the N-3" position were investigated. The structure-activity relationships between the antiviral activity and the substituent at the N-3" position is described. In this series, 3"-N-acetyl-1-N-palmitoyl-kanamycin A (7c) showed the excellent antiviral activity against HSV-I and influenza virus. Further, we examined the synthesis and the antiviral activity of 3"-N-glycylkanamycin A derivatives (9) having a higher-acyl group at the N-1 position. The 3"-N-glycyl-1-N-pentadecanoylkanamycin A (9a) also exhibited excellent antiviral activity.