Title
Sinteza, identifikacija i spektralna karakterizacija odabranih jodovanih derivata prirodnih proizvoda
Creator
Đorđević, Miljana 1987-
Copyright date
2019
Object Links
Select license
Autorstvo-Nekomercijalno-Bez prerade 3.0 Srbija (CC BY-NC-ND 3.0)
License description
Dozvoljavate samo preuzimanje i distribuciju dela, ako/dok se pravilno naznačava ime autora, bez ikakvih promena dela i bez prava komercijalnog korišćenja dela. Ova licenca je najstroža CC licenca. Osnovni opis Licence: http://creativecommons.org/licenses/by-nc-nd/3.0/rs/deed.sr_LATN. Sadržaj ugovora u celini: http://creativecommons.org/licenses/by-nc-nd/3.0/rs/legalcode.sr-Latn
Language
Serbian
Cobiss-ID
Theses Type
Doktorska disertacija
description
Datum odbrane: 27.02.2020.
Other responsibilities
mentor
Radulović, Niko 1981-
član komisije
Ranđelović, Pavle 1980-
predsednik komisije
Stojanović, Gordana 1960-
član komisije
Sladić, Dušan 1958-
Academic Expertise
Prirodno-matematičke nauke
Academic Title
-
University
Univerzitet u Nišu
Faculty
Prirodno-matematički fakultet
Group
Odsek za hemiju
Alternative title
Synthesis, identification and spectral characterization of selected derivatives of natural products containing iodine
Publisher
[M. R. Đorđević]
Format
235 listova
description
Biobibliografski podaci: listovi 230-235;
Bibliografija: str. 196-215.
description
Organic and medicinal chemistry, organic synthesis and biochemistry
Abstract (en)
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).
Authors Key words
Organska sinteza, spektralna karakterizacija, jodovanje, aristol,
atropizomerija, „zelena sinteza“
Authors Key words
Organic synthesis, spectral characterization, iodination, aristol,
atropisomerism, green synthesis
Classification
547-302:[54.057/.058 + 543.429.23(043.3)
Subject
P 390, P 004
Type
Tekst
Abstract (en)
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).
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