Naslov (srp)

Sinteza, identifikacija i spektralna karakterizacija odabranih jodovanih derivata prirodnih proizvoda

Autor

Đorđević, Miljana 1987-

Doprinosi

Radulović, Niko 1981-
Ranđelović, Pavle 1980-
Stojanović, Gordana 1960-
Sladić, Dušan 1958-

Opis (eng)

The aims of this Ph.D. thesis were the synthesis, identification and spectral characterization of selected iodinated aromatic compounds which are either of natural origin or prepared by iodination of natural compounds. The structure of aristol, prepared by iodination of thymol under alkaline condition, was elucidated using modern chromatographic and extensive spectral techniques (NMR/FTIR/MS/UV), combined with chemical transformations and quantum mechanical calculations. A number of additional aristol constituents were identified by the use of a QSPR model (readily available structure-derived descriptors used to predict gas chromatographic retention data), in combination with mass spectrometry, directly from the aristol matrix without preparative chromatography. Formation mechanisms of aristol constituents were proposed. Several iodinated and brominated carvacrol derivatives were synthesized and their NMR analysis revealed that some of them exist as atropisomers - this is the result of a hindered rotation around a sp2-sp3 bond. Esters and ethers of diiodo- and dibromocarvacrols, as well as mixed bromoiodo derivatives were prepared and spectrally characterized and the presence of diastereomeric atropisomerism was observed for all compounds. A new synthesis of a natural product N-[2-(3,5-diiodo-4-methoxyphenyl)ethyl]benzamide, isolated from the ascidian Didemnum rubeum, and its analogs (formamide, benzamide, and acetamide) was accomplished. In order to perform an eco-friendly synthesis of N-acyl tyramines, with better yields and under milder reaction conditions, and in accordance with the principles of green chemistry, a solvent-free synthesis of D. rubeum natural product and other amides was developed. Some of the tyramides were tested for their toxicological/pharmacological activities, and these compounds showed different levels of toxicity towards Artemia salina. The tested compounds were rather non-toxic towards rat macrophages, but they affected their function (the activity of myeloperoxidase).

Opis (srp)

Biobibliografski podaci: listovi 230-235;Bibliografija: str. 196-215. Datum odbrane: 27.02.2020. Organic and medicinal chemistry, organic synthesis and biochemistry

Jezik

srpski

Datum

2019

Licenca

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Creative Commons CC BY-NC-ND 2.0 AT - Creative Commons Autorstvo - Nekomercijalno - Bez prerada 2.0 Austria License.

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