Title
Kombinatorne biblioteke odabranih prirodnih i sintetskih biološki aktivnih estara
Creator
Mladenović, Marko Z. 1987-
Copyright date
2017
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: 18.05.2017.
Other responsibilities
mentor
Radulović, Niko 1981-
član komisije
Blagojević, Polina 1979-
član komisije
Novaković, Irena
član komisije
Todorović, Tamara
član komisije
Stojanović-Radić, Zorica
Academic Expertise
Prirodno-matematičke nauke
Academic Title
-
University
Univerzitet u Nišu
Faculty
Prirodno-matematički fakultet
Group
Odsek za hemiju
Alternative title
Combinatorial libraries of selected natural and synthetic biologically active esters
Publisher
[M. Z. Mladenović]
Format
554 listova
description
Organic chemistry and biochemistry
Abstract (en)
Herein, a successful identification and a means of arriving at (milli)gram quantities of the selected
natural esters was achieved through the application of a synthetic combinatorial approach (three
libraries with 171 constituents in total, among them 121 new compounds). As a result, new secondary
metabolites from Achillea falcata L. ((1R*,3S*,5R*)-sabinyl formate and tiglate), Achillea ageratifolia
(Sm.) Boiss. subsp. serbica (Nyman) Heimerl ((1R*,3S*,5R*)-sabinyl formate, tiglate, nonanoate and
decanoate), Scandix balansae Reut. ex Boiss. (octadecyl valerate), Scandix pecten-veneris L. (esters of
isobutanoic acid and n-C15, C17, C21 and C23 alkanols, as well as esters of isovaleric acid and n-C13, C15
and C17 alkanols) and Anthemis segetalis Ten. (eugenyl angelate, 2-methylbutanoate and 3-
methylbutanoate) essential-oil samples wеre identified. Also, the combinatorial approach was successful
used for a systematical comparison of chemical/biological properties of ferrocene-containing esters and
their corresponding phenyl analogs (a library of eighteen (13 new) 2-substituted methyl acetoacetates).
The structures of the synthesized esters were spectrally characterized by MS, NMR (1D- and 2D-NMR,
as well as, an NMR methodology that employ lanthanide-induced shifts), FTIR and UV-Vis analyses,
and in the case of ferrocene-containing compounds by electrochemical (cyclic voltammetry) and X-ray
analyse(s). Several esters were shown to be toxic to A. salina, possessed cytotoxic (to two cell lines),
AChE inhibitory, antinociceptive and antimicrobial activities. Antinociceptive activity of
(1R*,3S*,5R*)-sabinol was two times higher than that of morphine, and the antifungal activity of 2-
acetyl-2-(ferrocenylmethyl)-4-methyl-4-pentenoate was comparable to that of nystatin against Candida
albicans.
Authors Key words
Organska sinteza, kombinatorne biblioteke estara, etarska ulja,
(1R*,3S*,5R*)-sabinol, dugolančani alkoholi, regioizomerni
alilmetoksifenoli, metil-2-(ferocenilmetil)acetoacetati, metil-2-
benzilacetoacetati, biološka/farmakološka aktivnost, QSPR
Authors Key words
Organic synthesis, combinatorial libraries of esters, (1R*,3S*,5R*)-sabinol, longchain
alkanols, regioisomeric allylmethoxyphenols, methyl-2-benzylacetoacetates,
methyl-2-(ferrocenylmethyl)acetoacetates, essential oils, biological/pharmacological
activity, QSPR
Classification
543.632.514.3 + 547.1-3](043.3)
Subject
P 390
Subject
P004
Type
Elektronska teza
Abstract (en)
Herein, a successful identification and a means of arriving at (milli)gram quantities of the selected
natural esters was achieved through the application of a synthetic combinatorial approach (three
libraries with 171 constituents in total, among them 121 new compounds). As a result, new secondary
metabolites from Achillea falcata L. ((1R*,3S*,5R*)-sabinyl formate and tiglate), Achillea ageratifolia
(Sm.) Boiss. subsp. serbica (Nyman) Heimerl ((1R*,3S*,5R*)-sabinyl formate, tiglate, nonanoate and
decanoate), Scandix balansae Reut. ex Boiss. (octadecyl valerate), Scandix pecten-veneris L. (esters of
isobutanoic acid and n-C15, C17, C21 and C23 alkanols, as well as esters of isovaleric acid and n-C13, C15
and C17 alkanols) and Anthemis segetalis Ten. (eugenyl angelate, 2-methylbutanoate and 3-
methylbutanoate) essential-oil samples wеre identified. Also, the combinatorial approach was successful
used for a systematical comparison of chemical/biological properties of ferrocene-containing esters and
their corresponding phenyl analogs (a library of eighteen (13 new) 2-substituted methyl acetoacetates).
The structures of the synthesized esters were spectrally characterized by MS, NMR (1D- and 2D-NMR,
as well as, an NMR methodology that employ lanthanide-induced shifts), FTIR and UV-Vis analyses,
and in the case of ferrocene-containing compounds by electrochemical (cyclic voltammetry) and X-ray
analyse(s). Several esters were shown to be toxic to A. salina, possessed cytotoxic (to two cell lines),
AChE inhibitory, antinociceptive and antimicrobial activities. Antinociceptive activity of
(1R*,3S*,5R*)-sabinol was two times higher than that of morphine, and the antifungal activity of 2-
acetyl-2-(ferrocenylmethyl)-4-methyl-4-pentenoate was comparable to that of nystatin against Candida
albicans.
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