NUCLEOSIDES AND NUCLEOTIDES .132. SYNTHESIS AND BIOLOGICAL EVALUATIONS OF RING-EXPANDED OXETANOCIN ANALOGS - PURINE AND PYRIMIDINE ANALOGS OF 1,4-ANHYDRO-2-DEOXY-D-ARABITOL AND 1,4-ANHYDRO-2-DEOXY-3-HYDROXYMETHYL-D-ARABITOL

)-2-C-(Adenin-9-yl)-1,4-anhydro-2-deoxy-D-arabitol (2) and (2R, 4-anhy dro-2,3-dideoxy-3-C-hydroxymethyl-D-arabitol (3), and their 2,6-diamin opurine analogues 4 and 5 were synthesized from corresponding 1,4-anhy dro-D-ribitol derivatives, which were readily obtained from D-glucose. The corresponding guanine isonucleosides 6 and 7 were obtained from 4 and 5 by enzymatic deamination with adenosine deaminase. Pyrimidine c ounterparts 8 and 9 were synthesized via construction of the pyrimidin e moiety from amino derivatives of the 1,4-anhydro-D-arabitol derivati ves. Antiviral activity of these ring-expanded derivatives of oxetanoc ins towards HSV-1, HSV-2, HCMV, and HBV in vitro was examined along wi th their cytotoxicity against L1210 and KB cells in vitro.