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Australian Journal of Chemistry Australian Journal of Chemistry Society
An international journal for chemical science
RESEARCH ARTICLE

Purine Analogues as Amplifiers of Phleomycin. VI. The Synthesis and Metabolism of Some Benzothiazole, Benzoxazole and s-Triazolopyrimidine Amplifiers

DJ Brown and Y Iwai

Australian Journal of Chemistry 32(12) 2727 - 2733
Published: 1979

Abstract

The metabolisms of four 14C-tagged amplifiers of phleomycin are followed in mice. 2-(Benzothiazol- 2'-ylthio)acetamide (1c) gives mainly the corresponding acid (1e) in the urine; 2-(benzoxazol-2'- ylthio)acetamide (1d) likewise gives the acid (1f); N-methyl-2-(s-triazolo[4,3-a]pyrimidin- 3'-ylthio)propionamide (2b) gives unchanged material (c. 20%) plus not the corresponding acid (2c), but its [1,5-a] isomer (3c) in 60% yield; and 2-(5',7'-diethyl-s-triazolo[4,3- a]pyrimidin-3'-ylthio)-acetamide (2i) proves much more stable by giving mainly unchanged material (>60%). Minor metabolites are formed in each case.    

Syntheses and N.M.R. spectra of the above substrates and related derivatives are reported as well as their activities as amplifiers of phleomycin against in vitro cultures of Escherichia coli.

https://doi.org/10.1071/CH9792727

© CSIRO 1979

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