Synthesis and antiviral activities of carbocyclic oxetanocin analogues.
9-Cyclobutyladenine (4a), cis- and trans-9-[3- (hydroxymethyl)cyclobutyl]adenine (4b) and 9-[3,3-bis(hydroxymethyl)cyclobutyl]adenine(4d) were prepared from the corresponding cyclobutylamine derivatives (1a, 1b and 1d). Guanine congeners (9a, cis- and trans-9b and 9d) and carbocyclic oxetanocin G (1',2'-trans-9f) were also prepared. Carbocyclic oxetanocin A(1',2'-trans-4f), the preparation of which we have already published, and G were found to be active against herpes simplex virus (type 1 and 2) in vitro, while cis-4b and cis-9b showed an in vitro antiretroviral activity against human immunodeficiency virus (type 1).
Maruyama
T
T
Faculty of Pharmaceutical Sciences, Tokushima Bunri University, Japan.
Sato
Y
Y
Horii
T
T
Shiota
H
H
Nitta
K
K
Shirasaka
T
T
Mitsuya
H
H
Honjo
M
M
D000225:Adenine / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000494:pharmacology; D000818:Animals; D000998:Antiviral Agents / Q000138:chemical synthesis* / Q000494:pharmacology; D003588:Cytopathogenic Effect, Viral / Q000187:drug effects; D006678:HIV / Q000187:drug effects; D018139:Simplexvirus / Q000187:drug effects; D014709:Vero Cells
D000998:Antiviral Agents; C051061:oxetanocin; D000225:Adenine