5--deoxyadenosine and aristeromycin

Using the observation that the side effects of aristeromycin (carbocyclic adenosine) were reduced by removing the methylene at the center in aristeromycin where phosphorylation occurs, derivatives of carbocyclic oxetanocin A (4a), oxetanocin G (4b), and 2-aminooxetanocin A (16) lacking the 3'-methylene have been prepared in racemic form. The only viruses for which an appreciable inhibitory effect of the compounds (minimum inhibitory concentration ranging from 1 to 40 microg/mL) was noted were herpes simplex virus type 1 (HSV-1) and varicella-zoster virus (VZV). However, when directly compared for their antiviral potency against HSV-1 with their parents oxetanocin A and oxetanocin G, compounds 4a and 4b proved clearly less active.

Topics: Adenine; Adenosine; Animals; Antiviral Agents; Cells, Cultured; Giant Cells; Guanine; Herpesvirus 1, Human; Herpesvirus 3, Human; HIV-1; HIV-2; Humans; Magnetic Resonance Spectroscopy; Molecular Structure; Viruses