Studies on antiviral agents. II. Synthesis and in vitro antiviral activity on new kanamycin A derivatives having higher acyl group at N-1 position.
The synthesis and antiviral activity of 3''-N-trifluoroacetylkanamycin A derivatives (6) having higher acyl group at the N-1 position are described. On the basis of the structure-activity relationships between antiviral activity and alkyl chain length in an acyl group at the N-1 position, analogs (6f approximately I) having higher alkylcarbonyl group exhibited antiviral activity against not only HSV-I but also influenza virus. Analogs (6q approximately v) having higher alkyloxycarbonyl group showed antiviral activity against HSV-I. In addition, kanamycin A derivatives (6n, o, y, z) possessing higher alkylcarbonyl group with a functional group, higher alkylaminocarbonyl group, and higher alkylthiocarbonyl group had antiviral activity against HSV-I. The analog (6h) showed a broad antiviral spectrum against both DNA (HSV-I, HSV-II, VZV) and RNA (influenza) viruses.
D000998:Antiviral Agents / Q000138:chemical synthesis* / Q000494:pharmacology; D007612:Kanamycin / Q000138:chemical synthesis* / Q000494:pharmacology; D009975:Orthomyxoviridae / Q000187:drug effects; D018139:Simplexvirus / Q000187:drug effects; D013329:Structure-Activity Relationship
D000998:Antiviral Agents; D007612:Kanamycin