Chemical & Pharmaceutical Bulletin 1990-10-01

Synthesis and antiviral activities of carbocyclic oxetanocin analogues.

T Maruyama, Y Sato, T Horii, H Shiota, K Nitta, T Shirasaka, H Mitsuya, M Honjo

Index: Chem. Pharm. Bull. 38(10) , 2719-25, (1990)

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Abstract

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).