Heterocyclic analogs of nucleosides: Synthesis and biological evaluation of some 1-(3-thianyl)uracil and 9-(3-thianyl)adenine derivatives

Article abstract of DOI:10.1139/v94-032

The 1-(3-thianyl)uracil (9) and 9-(3-thianyl)adenine (14) nucleoside analogs have been prepared from the key intermediate, (±)-(3β,5β)-3-amino-5-(hydroxymethyl)thinae (6). Analog 9 was converted into a mixture of diastereomeric sulfoxides (10) that afforded, by a Pummerer reaction, a mixture of (±)-1-{(2'β,3'β,5'β)-2'-acetoxy-5'-(acetoxymethyl)thian-3'-yl}2, 4(1H,3H)-pyrimidinedione (11a) and its 6'-β isomer (11b). The EI mass spectra of the nucleoside analogs are discussed. The uracil nucleoside analogs have been evaluated also for their anti-HIV and antitumor activities.