
TY  - JOUR
A1  - Brown, DJ 
A1  - Dunlap, WC 
A1  - Grigg, GW 
A1  - Kelly, J 
T1  - Thiazolo[5,4-d]pyrimidine derivatives as amplifiers of phleomycin against <I>Escherichia coli</I>
JF  - Australian Journal of Chemistry
JO  - Aust. J. Chem.
Y1  - 1977
VL  - 30
IS  - 8
SP  - 1775
EP  - 1783
KW  - 
UR  - https://doi.org/10.1071/CH9771775 
N2  - The acetylation of 5-amino-6-methylpyrimidine-2,4-dithione (1; R = H) followed by cyclo-dehydration gave 2,7-dimethylthiazolo[5,4-d] pyrimidine-5-thione (2; R = Me) which underwent S-alkylation by methyl iodide, 2-chloroacetamide, etc, to afford the corresponding 5-alkylthio derivatives (4a-c). Treatment of the same substrate with carbon disulphide provided 7-methyl-thiazolo[5,4-d]pyrimidine-2,5-dithione (6) and thence the corresponding 2,5-bisalkylthio derivatives (4d-g). Similar reactions with 5-amino-6-mercapto-2-methylpyrimidine-4- thione(5; R1 = Me, R2 = SH, R3 = H) gave 7-alkylthio-2,5- dimethylthiazolo[5,4-d]pyrimidines (4h-p) and 2,7-bis-alkylthio-5- methylthiazolo[5,4-d]pyrimidines [(4q) and (4r)]. Two 2-alkylthio-7- methoxythiazolo-[5,4-d]pyrimidines, (4s) and (4t), were made by similar methods.     The foregoing compounds were tested in vitro as amplifiers of phleomycin against E. coli. Some of the more soluble compounds showed activities comparable with those of the best purine amplifiers previously tested. 
ER  -

