2-Alkyloxyalkylthiohypoxanthines as new potent inhibitors of xanthine oxidase.
The title compounds were prepared and tested as xanthine oxidase (XO) inhibitors. Results evidenced that potency was related to the position of the oxygen atom in the 2-linear chain and that it grew with distance from the sulfur atom until it became equipotent to 2-n-hexylthiohypoxanthine. Enzymatic oxidation on C(2) occurred in the 8-alkylthiohypoxanthines. On the contrary, oxidation on C(8) did not occur in the 2-alkythioderivatives, demonstrating that the chain forced these molecules to form a complex with molybdenum(VI) involving only the N(3) and N(9) nitrogen atoms.
Biagi
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Dipartimento di Scienze Farmaceutiche, Università di Pisa, Italy.
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D004791:Enzyme Inhibitors / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D007042:Hypoxanthines / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D015394:Molecular Structure; D013057:Spectrum Analysis; D014969:Xanthine Oxidase / Q000037:antagonists & inhibitors*; D014970:Xanthines / Q000031:analogs & derivatives / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology
C453100:8-hexylthio-hypoxanthine; C453099:8-hexylthio-xanthine; D004791:Enzyme Inhibitors; D007042:Hypoxanthines; D014970:Xanthines; D014969:Xanthine Oxidase