title: Synthesis of the derivatives of 6-amino-uracil labelled with14C.
abstract: The radioactively labelled 6-amino-5-nitroso-uracil (1) and 5-acetyl-6-amino-1,3-dimethyl-uracil (2) were required for metabolic studies to assess their suitability as drug candidates. A common precursor for both compounds was [cyano-14C]cyanoacetic acid (6), readily prepared from potassium [14C]cyanide. ACS reagents, namely, diethyl ether, acetic acid and acetic anhydride, had to be rigorously repurified to achieve a successful synthesis of14C-labelled compounds on a tenth-of-a-milligramme scale. 6-Amino-5-nitroso-[6-14C]uracil (1-14C) (0.55 mCi) was prepared with radiochemical purity > 98% and specific activity (SA) = 55.6 mCi/mmol. 5-Acetyl-6-amino-1,3-dimethyl-[6-14C]uracil (2-14C) (8 mCi) was prepared with radiochemical purity > 97% and SA = 55.6 mCi/mmol. It has been shown that a SA assay can be made from standard13C NMR spectra, thus avoiding the need to perform lengthier inverse-gated13C NMR experiments.
authors.affiliation: Institute of Organic Chemistry and Biochemistry of CAS, Flemingovo nám. 2, 16610, Prague 6, Czech Republic.
authors.forename: Tomáš
authors.initials: T
authors.lastname: Elbert
authors.affiliation: Institute of Organic Chemistry and Biochemistry of CAS, Flemingovo nám. 2, 16610, Prague 6, Czech Republic.
authors.forename: Petr
authors.initials: P
authors.lastname: Hezký
authors.affiliation: Institute of Organic Chemistry and Biochemistry of CAS, Flemingovo nám. 2, 16610, Prague 6, Czech Republic.
authors.forename: Petr
authors.initials: P
authors.lastname: Jansa
mesh_terms: D000085:Acetates / Q000737:chemistry; D002250:Carbon Radioisotopes / Q000737:chemistry*; D060326:Chemistry Techniques, Synthetic; D007553:Isotope Labeling; D014498:Uracil / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry
chemical_list: D000085:Acetates; D002250:Carbon Radioisotopes; D014498:Uracil; C013400:6-aminouracil; C007170:cyanoacetic acid
keywords: 6-amino-uracil derivatives; [cyano-14C]cyanoacetic acid; carbon 14; specific activity assay