Synthesis and biochemical evaluation of nucleosides of naphthoquinone heterocycles.
The synthesis, characterization, and biochemical evaluation of 1-beta-D-ribofuranosylnaphtho[2,3-d]imidazole-4,9-dione (3), 2-beta-D-ribofuranosylnaphtho[2,3-d]pyrazole-4,9-dione (6), and 2-beta-D-ribofuranosylnaphthol[2,3-d]triazole-4,9-dione (9) are reported. These quinone nucleosides and the corresponding quinone heterocycles were tested as inhibitors of purine nucleotide biosynthesis in Ehrlich ascites cells. The nucleosides 3 and 9 and naphtho[2,3-d]imidazole-4,9-dione were effective inhibitors of hypoxanthine phosphoribosyltransferase.
D000818:Animals; D002286:Carcinoma, Ehrlich Tumor / Q000201:enzymology / Q000378:metabolism; D003864:Depression, Chemical; D007041:Hypoxanthine Phosphoribosyltransferase / Q000037:antagonists & inhibitors; D066298:In Vitro Techniques; D009682:Magnetic Resonance Spectroscopy; D009285:Naphthoquinones / Q000138:chemical synthesis* / Q000494:pharmacology; D011685:Purine Nucleotides / Q000096:biosynthesis; D012263:Ribonucleosides / Q000138:chemical synthesis* / Q000494:pharmacology
D009285:Naphthoquinones; D011685:Purine Nucleotides; D012263:Ribonucleosides; D007041:Hypoxanthine Phosphoribosyltransferase