Synthesis and QSAR of thia-Derivatives of Aroylacrylic Acids

Syntheses of thirty-one aroylacrylic acids, twenty-seven 2-[(carboxymethyl)sulfanyl]-4-oxo-4-arylbutanoic acids (CSAB), three 2-[(2-carboxyethyl)sulfanyl]-4-oxo-4-arylbutanoic acids, one 2-[(1-carboxyethylsulfanyl]-4-oxo-4-arylbutanoic acid, one 2-[(2-methoxy-2-oxoethyl)sulfanyl]-4-oxo-4-arylbutanoic acid and one 2-ethoxycarbonylmethylsulfanyl]-4-oxo-4-arylbutanoic acid, are described. Conformational preferences of CSAB in polar and non-polar solvents, DMSO and chloroform, are examined. Analysis of conformational preferences in solution (NAMFIS analysis) is performed, using 1H NMR, NOESY, J-HMBC spectra, and conformational assemblies of compound obtained by CS in Macro Model and OMEGA. Most abound conformers in non-polar chloroform have an extended shape - largest part of apolar surface area of molecules are exposed to solvent. Advantages of methods based on 3D structure of compounds for the estimation of n-octanol/water partition coefficients (logP values) are briefly outlined. In extended conformations divalent S atom could form non-covalent intermolecular interactions with other heteroatoms (O, N) in closest proximity.

Ivan Juranic is retired professor of the Faculty of Chemistry, University of Belgrade, Serbia. He is still active in research and in coaching of PhD students. He has over 150 published research papers, and several patents. I. Juranic is section editor of the Journal of the Serbian Chemical Society, and is referee in many other scientific Journals.