Synthesis, chemistry, and biological activity of 5 thiocyanatopyrimidine nucleosides as potential masked thiols

Article abstract of DOI:10.1021/jm00250a006

The reaction of chlorothiocyanogen (ClSCN) with various derivatives of uracil was investigated as potential route to 5 mercaptouracils. Reaction of 1,3 dimethyluracil, 1 (β D ribofuranosyl)uracil, 1 (2' deoxy β D ribofuranosyl)uracil, 1 (β D arabinofuranosyl)uracil, 1 (2',3',5' tri O chloroacetyl β D ribofuranosyl)uracil, and 1 (2',3',5' tri O acetyl β D ribofuranosyl)uracil with ClSCN in acetic acid gave the corresponding 5 thiocyanato derivatives in fair to excellent yields. These 5 thiocyanatopyrimidine nucleosides can be reduced by dithiothreitol, sodium dithionite 2 mercaptoethanol, or glutathione to the biologically active 5 mercaptopyrimidine nucleosides. The intermediate 5 thiocyanatopyrimidine nucleosides show significant biological activity, probably as the result of in vivo reduction.