Partition Property of 5-Nitrothiopyrimidine Nucleoside

摘要

5-Nitrouracil and 5-nitrouridine derivatives which C-2 and C-4 oxo-groups of the pyrimidine base were replaced by thio groups were synthesized. The lipophilicities of thiopyrimidine bases were enhanced significantly as indicated by P-values. Oxygen-sulfur exchange leading to 2-thiouracil (2) and 2,4-dithiouracil (3) were associated with 1.4- and 2.6-fold increase in P-value relative to that of uracil (1). The P-values of 5-nitro-2-thiouracil (5) and 5-nitro-2,4-dithiouracil (6) were increased 13.2- and 79.8-fold relative to that of 5-nitrouracil (4). Most of the 5-nitrothiopyrimidine bases and their nucleosides were found to be moderately active against Staphylococcus aureus and Escherichia coli except 5-nitrouracil (4).