Nucleosides and nucleotides. 132. Synthesis and biological evaluations of ring-expanded oxetanocin analogues: Purine and pyrimidine analogues of 1,4-anhydro-2-deoxy-D-arabitol and 1,4-anhydro-2-deoxy-3-hydroxymethyl-D-arabitol

Article abstract of DOI:10.1016/S0040-4020(01)81749-X

(2R)-2-C-(Adenin-9-yl)- 1,4-anhydro-2-deoxy-_D-arabitol (2) and (2R, 3R)-2-C-(adenin-9-yl)- 1,4-anhydro- 2,3-dideoxy-3-C-hydroxymethyl-_D-arabitol (3), and their 2,6-diaminopurine analogues 4 and 5 were synthesized from corresponding 1,4-anhydro-_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 counterparts 8 and 9 were synthesized via construction of the pyrimidine moiety from amino derivatives of the 1,4-anhydro-_D-arabitol derivatives. Antiviral activity of these ring-expanded derivatives of oxetanocins towards HSV-1, HSV-2, HCMV, and HBV in vitro was examined along with their cytotoxicity against L1210 and KB cells in vitro.