National Repository of Grey Literature 2 records found  Search took 0.00 seconds. 
Synthesis and biological properties of polysubstituted 5-nitrosopyrimidines
Janeba, Zlatko ; Čechová, Lucie ; Žurek, Jiří ; Procházková, Eliška ; Dračínský, Martin
2,4,6-Triamino-5-nitrosopyrimidines have been reported to contain a strong intramolecular hydrogen bond between the 5-nitroso and 4- or 6-amino groups, thus forming an additional pseudoring. Such analogues were speculated to be good mimics of fused bicyclic derivatives, e.g. purines. A series of novel polysubstituted 2-amino-5-nitrosopyrimidines, as potential structural mimics of modifi ed purine nucleos(t)ides well-known for their important biological properties, has been designed and synthesized. The physicochemical and biological properties of the prepared polysubstituted 2-amino-5-nitrosopyrimidines are being evaluated.
Switchable intramolecular hydrogen bond in polysubstituted 5-nitrosopyrimidines
Procházková, Eliška ; Čechová, Lucie ; Žurek, Jiří ; Janeba, Zlatko ; Dračínský, Martin
The formation of strong intramolecular hydrogen bonds was observed in a series of 2-amino-5-nitrosopyrimidines with alkylamino and arylamino substituents in the positions 4 and 6. Mixtures of two rotamers differing in the orientation of the nitroso group were observed in the NMR spectra of the compounds where two distinct intramolecular hydrogen bonds could be formed. In several cases, we were able to isolate and characterize the two hydrogen bond isomers (two conformers) by column chromatography. The ratio of the two rotamers in equilibrium depends strongly on the character of the substituents in the positions 4 and 6 and can be finely tuned in a broad range of conformation ratios. The experimental results were supported by DFT calculations.

Interested in being notified about new results for this query?
Subscribe to the RSS feed.