Author, institution: Rita Vaickelionienė, Kaunas University of Technology
Science area, field: Physical Siences, Chemistry
The Doctoral Dissertation is available at the library of Kaunas University of Technology (K. Donelaičio St. 20, Kaunas).
Scientific Supervisor: Prof. Dr. Habil. Vytautas MICKEVIČIUS (Kaunas University of Technology, Physical Sciencies, Chemistry – 03P)
Dissertation defence board of Chemistry Science Field:
Prof. Dr. Habil. Algirdas ŠAČKUS (Kaunas University of Technology, Physical Sciencies, Chemistry – 03P) – chairman;
Assoc. Prof. Dr. Svajūnas ASADAUSKAS (Center for Physical Sciences and Technology, Institute of Chemistry, Physical Sciencies, Chemistry – 03P);
Dr. Sergej BELYAKOV (Latvian Institute of Organic Synthesis, Riga, Latvia, Physical Sciencies, Chemistry – 03P);
Prof. Dr. Vytautas GETAUTIS (Kaunas University of Technology, Physical Sciencies, Chemistry – 03P);
Prof. Dr. Habil. Sigitas TUMKEVIČIUS (Vilnius University,Physical Sciencies, Chemistry – 03P).
Annotation:
The incorporation of fluorine into organic molecules can dramatically alter their reactivity, chemical and biological properties, and physiological activity. Fluorine can exert major influence on the acidity or basicity of functional groups. It may also change the molecular conformation and it generally increases the stability of hydrocarbons. For instance, fluorine substituents have been shown to affect the metabolic stability, lipophilicity, and the binding affinity of many drugs. These unique properties that fluorine substitution can produce in pharmaceuticals, agrochemicals, and materials have led to an increased interest in fluorine chemistry.
The main aim of the work: synthesis of new, potentially biologically active fluorine-containing N-aryl-β– and β,γ–amino acids, their derivatives and cyclization products, and the investigation of the structure and characteristics of the synthesized compounds.
A new approach to the synthesis of 1-substituted dihydropyrimidin-2,4(1H,3H)-diones or 2-thioxotetrahydropyrimidin-4(1H)-ones was proposed. The advantage of this method is the possibility to synthesize the above-mentioned heterocycles not only from b-amino acids, but also from their mixtures with 3-[(substituted phenyl)(2-carboxyethyl)amino]propanoic acids as well as from the latter compounds. For the first time 3-[(4-fluorophenyl)carbamothioylamino]propanoic acid was used for the synthesis of compounds containing thiazole, thiazole and chalkone, condensed thiazolo[4,5-b]quinoxalinyl and 4,9-dioxo-4,9-dihydronaphtho[2,3-d]thiazolyl fragments with an unchanged carboxyalkyl chain in the molecule. The biological properties of these compounds were investigated. Studies of the antimicrobial activity of the synthesized compounds revealed potentially new compounds with antibacterial activity against Staphylococcus aureus and Mycobacterium luteum.
The possibility to synthesize hydrazones, pyrrole, pyrazole, oxadiazole, aminotriazole and azine derivatives based on 1-(substituted phenyl)-5-oxopyrrolidine-3-carboxylic acid hydrazides was investigated. 1-(4-fluoro and 3-trifluoromethylphenyl)-5-oxopyrrolidine-3-carboxylic acids were used for the formation of the benzimidazole fragment containing derivatives. Various chemical transformations of the synthesized benzimidazoles were carried out.
