Synthesis of 5-substituted uracil derivatives.
The synthesis of a series of 5-substituted uracil derivatives is described. 5-Bromoacetyluracil (2a) was converted to the glycolyl (2b), glycyl (2c), N,N-dimethylglycyl (2d), 4-imidazolyl (3), and 2-amino-4-thiazolyl (4) derivatives. 5-Formyluracil (5) was used in the preparation of the 2-imidazolyl (6), the 3-acrylic acid (7b), the ester (7a), and the 3-N,N-dimethylacrylamide (8) derivatives. A Mannich reaction converted 5-acetyluracil to the amino ketone 9 which was reduced to give the 3-dimethylamino-1-propanol derivative 10. Compounds 2b,d,3,4,6, and 7b failed to inhibit the growth of Escherichia coli B and Staphylococcus aureus.
D004926:Escherichia coli / Q000187:drug effects / Q000254:growth & development; D013211:Staphylococcus aureus / Q000187:drug effects / Q000254:growth & development; D014498:Uracil / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000494:pharmacology
D014498:Uracil