Development of a new xymedone production technology

Belyaev, P. G.; Khisamutdinov, G. Kh.; Sharypova, S. G.; Konovalova, V. P.; Kondyukov, I. Z.; Valeshnii, S. I.; Smirnov, S. P.; Ильин, В. П.

doi:10.1007/s11094-008-0090-1

Cited by 2 publications

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“…Two decades ago, xymedon (1,2‐dihydro‐4,6‐dimethyl‐1‐(2‐hydroxyethyl)‐2‐oxopyrimidine, 1 ) was discovered, an original burn treatment agent with immunostimulatory action . This structurally simple compound also features therapeutic effects for treatment of a variety of other diseases (hepatoprotective, actoprotective, and neuroregeneration stimulants).…”

Section: Introductionmentioning

confidence: 99%

Hydrogen's isotopic exchange reaction in the C‐methyl sides in the medicinal agent xymedon: NMR spectroscopy and ab initio calculations

Latypov

Kondrashova

Galyametdinova

et al. 2018

J of Physical Organic Chem

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The kinetics of intramolecular and intermolecular exchange processes in xymedon (1‐(2‐hydroxyethyl)‐4,6‐dimethyl‐1,2‐dihydropyrimidin‐2‐one, a regeneratory, wound‐healing drug) and its analogue were investigated in the solution. Hydrogen's mobility was detected in the C‐methyl sides of these compounds. This mobility was monitored via NMR in the hydrogen/deuterium exchange reaction in water. Two models were proposed as explanations for this hydrogen‐deuterium exchange. According to the main model, the key intermediates of these reactions are low‐energy tautomers of xymedon in which the N3 is protonated following which one proton leaves either 6‐Me or 4‐Me and thus its hybridization is changed. This hydrogen‐to‐deuterium exchange reaction is much faster under acidic conditions although it also occurs in alkaline conditions. Methylation via MeOTs or MeI leads to products with a quaternized ring N3 atom in which a hydrogen‐to‐deuterium exchange reaction also takes place, although the rates of the 6‐Me and 4‐Me hydrogens exchange are reversed. According to density functional theory calculations, the presence of methyl groups at the C4/C6 positions and of the C═O fragment is crucial to remarkably lower the energies of these “rare” tautomers. The exact position of the C═O in heterocycle is also very important in the tautomers' relative stability.

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Section: Introductionmentioning

confidence: 99%