Studies on the Synthesis and Biological Activities of 4'-(R)-Hydroxy-5'-(S)-hydroxymethyl-tetrahydrofuranyl Purines and Pyrimidines

Article abstract of DOI:10.1016/0968-0896(96)00048-X

A series of 4'-(R)-hydroxy-5'-(S)-hydroxymethyl-tetrahydrofuranyl purines and pyrimidines were synthesized by the reaction of 3,4-epoxy-5-(S,trans)-dimethoxymethyl-tetrahydrofuran and nucleobases under the catalysis of potassium tert-butoxide and 18-crown-6.Compounds 6a, 6c and 7b have shown significant inhibition on the growth of HL-60 cells.The phosphotriester and phosphodiester of isonucleoside 8a-d were synthesized and cytotoxic activities were reported.The conformation of isonucleosides in solution was studied by 1H NMR.Key words: isonucleoside; cytotoxicity; anti-HSV type I and HSV type II; conformation; stereochemistry.