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master's thesis
Priprava novih meta i para supstituiranih piridinonskih alfa-manozida i njihov antiadhezijski učinak
Zagreb: University of Zagreb, Faculty of Science, 2018. urn:nbn:hr:217:046696
Matišić, Mateja
University of Zagreb
Faculty of Science
Department of Chemistry

Institutional repository: Repository of the Faculty of Science

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Matišić, M. (2018). Priprava novih meta i para supstituiranih piridinonskih alfa-manozida i njihov antiadhezijski učinak (Master's thesis). Zagreb: University of Zagreb, Faculty of Science. Retrieved from https://urn.nsk.hr/urn:nbn:hr:217:046696

Matišić, Mateja. "Priprava novih meta i para supstituiranih piridinonskih alfa-manozida i njihov antiadhezijski učinak." Master's thesis, University of Zagreb, Faculty of Science, 2018. https://urn.nsk.hr/urn:nbn:hr:217:046696

Matišić, Mateja. "Priprava novih meta i para supstituiranih piridinonskih alfa-manozida i njihov antiadhezijski učinak." Master's thesis, University of Zagreb, Faculty of Science, 2018. https://urn.nsk.hr/urn:nbn:hr:217:046696

Matišić, M. (2018). 'Priprava novih meta i para supstituiranih piridinonskih alfa-manozida i njihov antiadhezijski učinak', Master's thesis, University of Zagreb, Faculty of Science, accessed 26 November 2024, https://urn.nsk.hr/urn:nbn:hr:217:046696

Matišić M. Priprava novih meta i para supstituiranih piridinonskih alfa-manozida i njihov antiadhezijski učinak [Master's thesis]. Zagreb: University of Zagreb, Faculty of Science; 2018 [cited 2024 November 26] Available at: https://urn.nsk.hr/urn:nbn:hr:217:046696

M. Matišić, "Priprava novih meta i para supstituiranih piridinonskih alfa-manozida i njihov antiadhezijski učinak", Master's thesis, University of Zagreb, Faculty of Science, Zagreb, 2018. Available at: https://urn.nsk.hr/urn:nbn:hr:217:046696

Metadata
TitlePriprava novih meta i para supstituiranih piridinonskih alfa-manozida i njihov antiadhezijski učinak
Title (english)Preparation of Novel meta and para Substituted Pyridinone alpha-Mannosides and their Anti-adhesion Activity
AuthorMateja Matišić
MentorVesna Petrović Peroković (mentor)
Committee memberVesna Petrović Peroković (predsjednik povjerenstva)
Committee memberSanda Rončević (član povjerenstva)
Committee memberBiserka Prugovečki (član povjerenstva)
Committee memberSrđanka Tomić-Pisarović (član povjerenstva)
GranterUniversity of Zagreb
Faculty of Science
(Department of Chemistry)
Zagreb
Defense date and country2018-02-23, Croatia
Scientific / art field,
discipline and subdiscipline		NATURAL SCIENCES
Chemistry
Abstract
U ovom diplomskom radu opisane su sinteze meta i para supstituiranih N-aril-3- hidroksipiridin-4-ona (3-7) i njihovih α-D-manozida (13-16). Piridinonski prekursori 3-7 priređeni su modificiranom Harrisovom metodom iz 5-benziloksipiran-4-on-2-karboksilne kiseline (2), dobivene iz komercijalno dostupne kojične kiseline, i odgovarajućih anilina (m- i p-metilanilina, m- i p-nitroanilina te m-metoksianilina) uz dodatak kiselog katalizatora (p- TsOH) zagrijavanjem u zatvorenoj teflonskoj posudi (autoklav). Spojevi 3-7 prevedeni su u acetilirane manozne derivate (8-11) pomoću 2,3,4,6-tetra-O-acetil-1-brom-α-D-manopiranoze uz AgOTf kao promotor i kolidin (Koenigs-Knorrova metoda glikozidacije). Uklanjanjem acetatnih skupina s manozne podjedinice spojeva 8-11 Zemplénovim postupkom priređene su ciljne molekule, N-aril-3-hidroksipiridin-4-onskih α-manozidi (13-16), kojima je ispitan inhibitorski učinak u procesu adhezije E. coli na stanice eritrocita. Strukture svih priređenih spojeva određene su spektroskopijom NMR (1H i 13C) i spektrometrijom masa (MS).
Abstract (english)
In this diploma thesis the syntheses of meta and para substituted N-aryl 3-hydroxypyridin-4- ones (3-7) and their α-D-mannosides (13-16) are described. Pyridinone precursors 3-7 were prepared by Harris method from 5-benzyloxypyran-4-one-2-carboxylic acid (2) and corresponding anilines (m- and p-methylaniline, m- and p-nitroaniline and m-methoxyaniline) with the addition of acid catalyst (p-TsOH) and heathing in a sealed Teflon container (autoclave). Compound 2 was synthesized from commercially available kojic acid. Acetylated mannose derivatives (8-11) were obtained by Koenigs-Knorr glycosidation using 2,3,4,6- tetra-O-acetyl-1-bromo-α-D-mannopyranose, collidine and AgOTf as promoter. The target compounds, N-aryl 3-hydroxypyridin-4-one α-mannosides (13-16), were prepared by removal of acetyl groups from mannose subunit in compounds 8-11 (Zemplén procedure). The inhibitory activity of target molecules 13-16 in the E. coli adhesion to erythrocyte cells was evaluated. The structures of all prepared compounds were determined by NMR (1H i 13C) spectroscopy and mass spectrometry (MS).
Keywords
Keywords (english)
Languagecroatian
URN:NBNurn:nbn:hr:217:046696
Study programmeTitle: Graduate university studies in chemistry; specializations in: Research programme
Course: Research programme
Study programme type: university
Study level: graduate
Academic / professional title: magistar/magistra kemije (magistar/magistra kemije)
Type of resourceText
File originBorn digital
Access conditionsOpen access
Embargo expiration date: 2020-02-23
Terms of useLicence In copyright icon
Created on2018-03-23 13:51:18