Abstract
Twenty-six selected compounds were investigated as inhibitors of xanthine oxidase, the enzyme that can also detoxify 6-mercaptopurine; these compounds consisted of 19 purines, four pyrimidines, two 8-azapurines, and one imidazole. Among the inhibitors that complexed to xanthine oxidase as well or better than the substrate, hypoxanthine, were thioguanine, adenine, and 6, 8-dihydroxy-2-methylthiopurine (XXVI). The larger 2-benzylthio-6, 8-dihydroxypurine (XXVII) was synthesized and found to inhibit equally as well as XXVI. Then 2-benzylthiohypoxanthine (XXVIII) and 8-benzylthiohypoxanthine (XXIX) were synthesized; these two compounds were complexed elevenfold and threefold better, respectively, to the enzyme than the substrate. Thus the enzyme showed bulk tolerance for the benzylthio group of XXVII-XXIX; the benzylthio group is a logical group for placement of electrophilic groups to give candidate active-site-directed irreversible inhibitors of xanthine oxidase.
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