class of novel 1,2,3-triazole functionalised quinoline-2,4-diones was
synthesized using multi-step reaction approach, starting with the synthesis of
suitable organic azides that served as precursors for introduction of the first
1,2,3-triazole ring to the quinoline-2,4-dione framework.
Afterwards, desirable bis-triazole esters were obtained by acetylation of
mono-triazole alcohols, subsequent introduction of propargyl group to the
position N1 of quinolone heterocycle, and finally employment of
copper(I)-catalysed »click« reaction using three different organic azides. Resulted
bis- as well as mono-triazole acetates were then deprotected using acidic
alcoholysis, while provided alcohols were further oxidized to suitable aldehydes
and carboxylic acids. While crystallization of synthesized compounds was
normally performed in case of mono-triazoles, it was seldom successful for
bis-triazole species. Consequently, quinolones with two 1,2,3-triazole rings were
purified mostly by silica-gel column chromatography. During the fulfilment of
outline transformation scheme, various reaction conditions and synthetic routes
were tested, monitored, and finally optimised. Apart from mainstream reaction
pathway, some focus was also devoted to a few accompanying transformations
that either highlighted interesting behaviour of the studied systems
(quinoline-2,4-dione ring cleavage), or could be exploited as an alternative
approach to anthranilic acid derivatives preparation.
Several synthesized materials were also evaluated for their potential
ligand-to-metal coordination abilities, as well as antimicrobial activities against
ten microbial strains, including bacteria, yeast and fungi. Additionally, their
potential photoprotective characteristics were also briefly examined. Regrettably,
no interesting physical properties or biological activities were detected for any of
the tested compounds.
The vast majority of results obtained throughout my doctoral studies and
presented in this dissertation, have already been published or will be published in
scientific journals with the impact factors.
| ISBN: | 978-80-7454-839-0 |
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| EAN: | 9788074548390 |
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| Počet stran |
55 stran |
| Datum vydání |
15. 07. 2019 |
| Pořadí vydání |
První |
| Jazyk |
anglický |
| Vazba |
e-kniha - pdf |
| Autor: |
David Milićević |
| Nakladatelství |
Univerzita Tomáše Bati ve Zlíně |
| Tématická skupina |
999 - nezařazeno |
| Neprodejná publikace. Publikaci je možné poptávat zde: Vydáno elektronicky - volně dostupné na http://hdl.handle.net/10563/43796 |
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