
TY  - JOUR
A1  - Brown, DJ 
A1  - Dunlap, WC 
A1  - Grigg, GW 
A1  - Danckwerts, L 
A1  - Nagamatsu, T 
T1  - Purine analogues as amplifiers of phleomycin. II. Some s-Triazolo[4,3-a]pyridines, s-Triazolo[4,3- or 1,5-a]pyrimidines and s-Triazolo[3,4-b]benzothiazoles
JF  - Australian Journal of Chemistry
JO  - Aust. J. Chem.
Y1  - 1978
VL  - 31
IS  - 2
SP  - 397
EP  - 404
KW  - 
UR  - https://doi.org/10.1071/CH9780397 
N2  - s-Triazolo[4,3-a]pyridine-3(2H)-thione (1b) undergoes S-alkylation to give derivatives such as 2-(s-triazolo[4,3-a]pyridin-2'-ylthio)acetamide (4c) which may be oxidized to the corresponding sulfoxide (4g) and sulfone (4h). Likewise, alkylation of 1-methyl-s-triazolo[4,3-a]pyridinium-3-thiolate (2b) yields 3-carbamoylmethylthio-1-methyl-s-triazolo[4,3-a]pyridinium chloride (3).     Similar treatment of s-triazolo[4,3-a]pyrimidine-3(2H)-thione (1c) leads to 2-(s-triazolo[4,3-a]-pyrimidin-3'-ylthio)acetamide (4j) and analogues, all of which undergo Dimroth-like rearrangement to their respective [1,5-a]-isomers (5), (6b) and analogues. 2-(s-Triazolo[3,4-b]benzothiazol-3'-ylthio)acetamide (9b) was also prepared from the corresponding thione (8).     Activities of the above compounds as amplifiers of phleomycin against E. coli are tabulated. The amide (4c) is highly active, non- toxic and resistant to metabolism. 
ER  -

