title: Studies on antiviral agents. III. Synthesis and in vitro antiviral activity of 1-N-higher-acyl-3"-N-functionalized acylkanamycin A derivatives.
abstract: 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.
mesh_terms: D000583:Amikacin / Q000031:analogs & derivatives*; D000998:Antiviral Agents / Q000138:chemical synthesis* / Q000494:pharmacology; D007612:Kanamycin / Q000031:analogs & derivatives*; D009975:Orthomyxoviridae / Q000187:drug effects; D018139:Simplexvirus / Q000187:drug effects; D013329:Structure-Activity Relationship
chemical_list: D000998:Antiviral Agents; D007612:Kanamycin; C013452:1-N-acylkanamycin B; D000583:Amikacin