Feskov I. 1,3-Substituted cyclobutanecarboxylic acids as structural fragments for isosteric replacements

1,3-substituted cyclobutane-containing compounds. Design of new promising 1,3-substituted cyclobutanecarboxylic acids and development of convenient preparative approaches to their synthesis, study of the main properties of synthesized compounds, as well as the effectiveness of their use for isosteric replacement. Organic synthesis, NMR spectroscopy on 1H, 13C, 19F, 2D NMR spectroscopy (NOESY), chromatographic methods of purification / separation of compounds, chromato-mass spectrometry, mass spectrometry, X-ray diffraction analysis. A preparative method for the synthesis of new bioisosteres of known GPR40 receptor ligands has been developed. A convenient preparative method for the synthesis of new alpha, gamma and delta amino acids - analogues of natural amino acids - has been developed. The physicochemical properties of the obtained compounds have been studied. Four 3-((hetera)cyclobutyl)azetidine-based isosteres of piperidine, piperazine, and morpholine were designed and synthesized. X-ray diffraction studies of the products obtained, followed by exit vector plot analysis of their molecular geometry demonstrated their larger size and increased conformational flexibility as compared to the parent heterocycles, and confirmed their potential utility as building blocks for lead optimization programs. Scope - organic, bioorganic and medical chemistry.