Carbocyclic oxetanocins lacking the C-3' methylene.
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.
Wu
J
J
Department of Chemistry, University of South Florida, Tampa 33620, USA.
Schneller
S W
SW
Seley
K L
KL
D000225:Adenine / Q000031:analogs & derivatives* / Q000737:chemistry / Q000494:pharmacology; D000241:Adenosine / Q000031:analogs & derivatives / Q000737:chemistry / Q000494:pharmacology; D000818:Animals; D000998:Antiviral Agents / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D002478:Cells, Cultured; D015726:Giant Cells / Q000187:drug effects; D006147:Guanine / Q000031:analogs & derivatives* / Q000737:chemistry / Q000494:pharmacology; D015497:HIV-1 / Q000378:metabolism; D015498:HIV-2 / Q000378:metabolism; D018259:Herpesvirus 1, Human / Q000187:drug effects; D014645:Herpesvirus 3, Human / Q000187:drug effects; D006801:Humans; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D014780:Viruses / Q000187:drug effects*
D000998:Antiviral Agents; C051061:oxetanocin; C057479:oxetanocin G; C060650:2-aminooxetanocin A; C030034:aristeromycin; D006147:Guanine; D000225:Adenine; D000241:Adenosine