engleski

Characterization of oximes containing heterocyclic aromatic and/or non-aromatic substructures

The better characteristics of compounds essential for their biological efficacy can be revealed by the systematic variations of their structure. For example, selectivity can be tuned by the modification of substituents or change of the base, usually heterocyclic moiety. Compounds which possess an oxime functionality (R1R2C=N-OH) usually have a broad scope of useful applications, equally in organic chemistry, materials science [1] as well as one in medicinal chemistry (e.g. treatment of acute intoxication by organophosphorus compounds [2]). Oximes containing heterocyclic aromatic (imidazole) and non-aromatic (quinuclidine) substructures as well as Cinchona alkaloid derivatives were synthesized. To quantify the effects of R1 and R2 group modifications, pKa values were measured and partition-coefficients determined. The variation of the substituents did not only result in the change of the molecular shape, but also had substantial impact on the acidity of the oxime hydroxyl group and basicity of the heterocyclic nitrogen atom. Molecular modelling was used to define conformational space of flexible compounds, to describe structural changes and determine electronic effects as a function of the group R. References [1] M. Skočibušić, R. Odžak, Z. Štefanić, I. Križić, L. Krišto, O. Jović, T. Hrenar, I. Primožič, D. Jurašin, Colloids and Surfaces. B, Biointerfaces 140 (2016) 548-559. [2] M. Katalinić, N. Maček Hrvat, K. Baumann, S. Morasi Piperčić, S. Makarić, S. Tomić, O. Jović, T. Hrenar, A. Miličević, D. Jelić, S. Žunec, I. Primožič, Z. Kovarik, Toxicology and Applied Pharmacology 310 (2016) 195-204.

oksimi ; heterocikli ; bazičnost

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