Synthesis of the derivatives of 6-amino-uracil labelled with C-14

0471547 - ÚOCHB 2017 RIV GB eng J - Journal Article
Elbert, Tomáš - Hezký, Petr - Jansa, Petr
Synthesis of the derivatives of 6-amino-uracil labelled with C-14.
Journal of Labelled Compounds and Radiopharmaceuticals. Roč. 59, č. 14 (2016), s. 615-618. ISSN 0362-4803. E-ISSN 1099-1344.
[International Isotope Symposium on the Synthesis and Applications of Isotopes and Isotopically Labelled Compounds /12./. Princeton, 07.06.2015-11.06.2015]
R&D Projects: GA MŠMT LG13002
Institutional support: RVO:61388963
Keywords : 6-amino-uracil derivatives * specific activity assay using NMR * [C-14]cyanoacetic acid
Subject RIV: CC - Organic Chemistry
Impact factor: 1.745, year: 2016

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-C-14] cyanoacetic acid (6), readily prepared from potassium [C-14]cyanide. ACS reagents, namely, diethyl ether, acetic acid and acetic anhydride, had to be rigorously repurified to achieve a successful synthesis of C-14-labelled compounds on a tenth-of-a-milligramme scale. 6-Amino-5-nitroso-[6-C-14] uracil (1-C-14) (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-C-14] uracil (2-C-14) (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 standard C-13 NMR spectra, thus avoiding the need to perform lengthier inverse-gated C-13 NMR experiments.
Permanent Link: http://hdl.handle.net/11104/0269008