Pyrimidine-2,4,6-triones

The first example in Figure 11.1 shows a pyrimidine trione compound bound to the active site of stromelysin. In order to get the interaction of one of the acidic pyrimidine nitrogens with the zinc cation correctly, the deprotonated negatively charged isomer has to be considered. 

Fig. 11.1 Protonation state example pyrimidine trione compound bound to stromelysin (PDB lg4k). Only the pyrimidine trione ring ofthe ligand is shown in 3D for clarity.

Another furan precursor 161 has been used to generate a series of pyrrolo[2,3-rf]pyrimidine triones 162 (Equation 60) the furandiones react with aryl isocyanates, releasing 2 mol of carbon dioxide, to form compounds 162a-f <2004ASJ877>. 

Barbiturates (pyrimidine triones such as 10.25) used to be widely used as sedatives, but have now largely been superseded by drugs with fewer side-effects. Suggest a synthesis of 10.25. 

Pentobarbital] (pyrimidine trione barbiturate) Synthetic GABAA-R agonist [anaesthetic, anticonvulsant used for euthanasia]... 

Sodium 5-allyl-5-(l-methyl butyl) barbiturate 2, 4, 6 (IH, 3H, 5H)-Pyrimidine-trione, 5-(l-methyl butyl)-5-(2-propenyl)-, monosodium salt Secobarbitone sodium. 

Synonyms 5-(l-Cyclohexen-l-yl)-5-ethyl-2,4,6(lH,3H,5H)-pyrimidine-trione 5-(l-cyclohexen-l-yl) 5-ethylbarbituric acid cyclobarbitone... 

Methyl-5-phenyl- 2,4,6(1//,3//,5/i)-pyrimidine- trione Phenylmethylbarbituric acid C11H10N2O3 76-94-8 218.208 cry 220 IH20 sEt0H, eth, alk... 

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