Synthesis of carbocyclic orotidine analogs as potential orotidine decarboxylase inhibitors.
An asymmetric synthesis of carbocyclic orotidine 15 and its monophosphate 16 were accomplished via the key intermediate cyclopentanone 4, which was prepared from D-gamma-ribonolactone in steps. None of synthesized the compounds inhibited orotidine 5'-monophosphate decarboxylase (EC 4.1.1.23) or orotate phosphoribosyltransferase (EC 2.4.2.10).
Song
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Department of Pharmaceutical and Biomedical Sciences, College of Pharmacy, The University of Georgia, Athens 30602, USA.
Naguib
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el Kouni
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Chu
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D000146:Acids, Carbocyclic / Q000737:chemistry; D000818:Animals; D001671:Biochemistry / Q000379:methods; D004791:Enzyme Inhibitors / Q000138:chemical synthesis* / Q000378:metabolism / Q000494:pharmacology*; D005260:Female; D006801:Humans; D008099:Liver / Q000187:drug effects / Q000201:enzymology; D051379:Mice; D008815:Mice, Inbred Strains; D009962:Orotate Phosphoribosyltransferase / Q000037:antagonists & inhibitors; D009964:Orotidine-5'-Phosphate Decarboxylase / Q000037:antagonists & inhibitors*; D013329:Structure-Activity Relationship; D014529:Uridine / Q000031:analogs & derivatives* / Q000737:chemistry
D000146:Acids, Carbocyclic; D004791:Enzyme Inhibitors; C008714:orotidine; D009962:Orotate Phosphoribosyltransferase; D009964:Orotidine-5'-Phosphate Decarboxylase; D014529:Uridine