An autoxidation study of C2 substituted pyrimidine amino reductones

The reactivity of 5‐aminouracil derivatives in the model reaction of autoxidation of styrene initiated by 2,2′‐azobis(2‐methylpropionitrile) was studied. Alkyl substituents at the 6‐position of the uracil ring have a significant effect on the kinetic parameters of inhibition. The N‐H bond dissociation energy calculated at the M06‐2X/MG3S and G4 levels of the theory does not agree with the experimental values of the rate constants. The transition state was calculated at the M05/MG3S level of theory for 1,3‐dimethyl‐5‐aminouracil, 1,3,6‐trimethyl‐5‐aminouracil, 1,3‐dimethyl‐6‐ethyl‐5‐aminouracil, 1,3‐dimethyl‐6‐isopropyl‐5‐aminouracil and 3‐butyl‐6‐methyl‐5‐aminouracil. The enthalpy of the transition state is in agreement with the experimental data and it can be used to evaluate the reactivity of the 5‐aminouracil derivatives with peroxyl radicals.

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Reactivity of 5‐aminouracil derivatives towards peroxyl radicals

Grabovskii

Andriyashina

Grabovskaya

et al. 2020

J of Physical Organic Chem

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Identification of novel chemotypes as CXCR2 antagonists via a scaffold hopping approach from a thiazolo[4,5-d]pyrimidine

Hoof

Boon

Loy

et al. 2022

European Journal of Medicinal Chemistry

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An autoxidation study of C2 substituted pyrimidine amino reductones

Cited by 2 publications

References 26 publications

Reactivity of 5‐aminouracil derivatives towards peroxyl radicals

Reactivity of 5‐aminouracil derivatives towards peroxyl radicals

Identification of novel chemotypes as CXCR2 antagonists via a scaffold hopping approach from a thiazolo[4,5-d]pyrimidine

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