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doctoral thesis
Priprava i karakterizacija bioaktivnih spojeva temeljenih na 1-azabiciklo[2.2.2]oktanu
Zagreb: University of Zagreb, Faculty of Science, 2019. urn:nbn:hr:217:662978
Radman Kastelic, Andreja
University of Zagreb
Faculty of Science
Department of Chemistry

Institutional repository: Repository of the Faculty of Science

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Radman Kastelic, A. (2019). Priprava i karakterizacija bioaktivnih spojeva temeljenih na 1-azabiciklo[2.2.2]oktanu (Doctoral thesis). Zagreb: University of Zagreb, Faculty of Science. Retrieved from https://urn.nsk.hr/urn:nbn:hr:217:662978

Radman Kastelic, Andreja. "Priprava i karakterizacija bioaktivnih spojeva temeljenih na 1-azabiciklo[2.2.2]oktanu." Doctoral thesis, University of Zagreb, Faculty of Science, 2019. https://urn.nsk.hr/urn:nbn:hr:217:662978

Radman Kastelic, Andreja. "Priprava i karakterizacija bioaktivnih spojeva temeljenih na 1-azabiciklo[2.2.2]oktanu." Doctoral thesis, University of Zagreb, Faculty of Science, 2019. https://urn.nsk.hr/urn:nbn:hr:217:662978

Radman Kastelic, A. (2019). 'Priprava i karakterizacija bioaktivnih spojeva temeljenih na 1-azabiciklo[2.2.2]oktanu', Doctoral thesis, University of Zagreb, Faculty of Science, accessed 20 November 2024, https://urn.nsk.hr/urn:nbn:hr:217:662978

Radman Kastelic A. Priprava i karakterizacija bioaktivnih spojeva temeljenih na 1-azabiciklo[2.2.2]oktanu [Doctoral thesis]. Zagreb: University of Zagreb, Faculty of Science; 2019 [cited 2024 November 20] Available at: https://urn.nsk.hr/urn:nbn:hr:217:662978

A. Radman Kastelic, "Priprava i karakterizacija bioaktivnih spojeva temeljenih na 1-azabiciklo[2.2.2]oktanu", Doctoral thesis, University of Zagreb, Faculty of Science, Zagreb, 2019. Available at: https://urn.nsk.hr/urn:nbn:hr:217:662978

Metadata
TitlePriprava i karakterizacija bioaktivnih spojeva temeljenih na 1-azabiciklo[2.2.2]oktanu
Title (english)Synthesis and characterization of bioactive compounds based on 1-azabicyclo[2.2.2]octane
AuthorAndreja Radman Kastelic
MentorInes Primožič (mentor)
Committee memberIva Juranović Cindrić (predsjednik povjerenstva)
Committee memberMaja Majerić-Elenkov (član povjerenstva)
Committee memberAnita Bosak (član povjerenstva)
GranterUniversity of Zagreb
Faculty of Science
(Department of Chemistry)
Zagreb
Defense date and country2019-11-29, Croatia
Scientific / art field,
discipline and subdiscipline		NATURAL SCIENCES
Chemistry
Universal decimal classification
(UDC)		54 - Chemistry. Crystallography. Mineralogy
Abstract
U okviru ove disertacije opisana je priprava 3-hidroksiimino-, 3-dodecilamino, 3- (N,N-dimetilkarbamoiloksi)-, 3-(N,N-dietilkarbamoiloksi), 3-(N-fenilkarbamoiloksi)-, te 3- (N,N-difenilkarbamoiloksi)kinuklidina, kao i 2-(kinuklidin-3-iliden)kinuklidin-3-ona i njegovog ketoksima. Spojevi su sintetizirani klasičnim postupcima organske sinteze, a ketoksim kinuklidina i mehanokemijskom sintezom. Ispitan je potencijal mehanokemijske sinteze oksima na nizu aldehida i ketona koji u svojoj strukturi imaju dušikove atome različite bazičnosti te je pokazano da su reakcije moguće uz katalitičku količinu otapala i bez dodatka baze. Nadalje, kvaternizacijom spojeva s metil-jodidom, but-3-en-1-il-bromidom i različito para i meta supstituiranim benzil-bromidima pripravljena su 42 derivata, od kojih 37 do sada nisu opisani u literaturi. Svi pripravljeni spojevi dobiveni su u zadovoljavajućem iskorištenju te im je struktura dokazana standardnim analitičkim metodama, a primjenjena je i spektroskopija nuklearne magnetske rezonancije za određivanje optičke čistoće kiralnih amina. Svi spojevi su pokazali bioaktivnost: oksimi i amini antibiotski potencijal, a karbamati inhibicijski potencijal prema kolinesterazama. Molekulskim modeliranjem određen je način vezanja N,N-dimetilkarbamata u aktivnom mjestu AChE.
Abstract (english)
In this thesis, the syntheses of 3-hydroxiimino-, 3-dodecylamino-, 3-(N,Ndimethylcarbamoyl) oxy-, 3-(N,N-diethylcarbamoyl)oxy-, 3-(N-phenylcarbamoyl)oxy-, 3- (N,N-diphenylcarbamoyl)oxyquinuclidine, as well as the condesation product of quinuclidine-3-on and its ketoxime are described. The possibility of mechanochemical synthesis (without the addition of external base and with catalytic amount of solvent) of oximes from carbonyl compounds that have nitrogen atoms of various bacisity was also determened. Furthermore, prepared compounds were quaternized with methyl iodide, but-3- en-1-yl bromide, and differently substituted meta and para benzyl bromides. 42 compounds were prepared in that manner, from which 37 for the first time. All compounds were prepared in good yields and were characterized by standard analytical methods. Bioactivity of compounds was tested. Oximes and amine derivatives showed antibacterial potential. The interaction of carbamates with cholinesterases was determined experimentaly and the mode of binding of 3-(N,N-dimethylcarbamates within the active site was determined.
Keywords
Keywords (english)
Languagecroatian
URN:NBNurn:nbn:hr:217:662978
Study programmeTitle: Doctoral study in chemistry
Study programme type: university
Study level: postgraduate
Academic / professional title: doktor/doktorica znanosti, područje prirodnih znanosti, polje kemija (doktor/doktorica znanosti, područje prirodnih znanosti, polje kemija)
Type of resourceText
Extent123 str. ; 30 cm
File originBorn digital
Access conditionsOpen access
Embargo expiration date: 2021-11-29
Terms of useLicence In copyright icon
Created on2020-01-29 12:03:27