Sinteza i biološka aktivnost novih azalidnih spojeva

master's thesis

• Title (english): Synthesis and biological activity of novel azalide compounds
• Author: Domagoj Džanko
• Mentor: Tatjana Gazivoda Kraljević (mentor)
• Mentor: Linda Tomašković (komentor)
• Committee member: Tatjana Gazivoda Kraljević (predsjednik povjerenstva)
• Committee member: Silvana Raić-Malić (član povjerenstva)
• Committee member: Linda Tomašković (član povjerenstva)
• Granter: University of Zagreb; Faculty of Chemical Engineering and Technology; Zagreb
• Defense date and country: 2023-09-28, Croatia
• Scientific / art field, discipline and subdiscipline: NATURAL SCIENCES; Chemistry

Abstract

Makrolidi predstavljaju dobro poznatu skupinu antibiotika, a karakterizira ih visoko supstituirani makrolaktonski prsten, aglikon, na koji su glikozidnom vezom vezani jedan ili više neutralnih ili aminošećera. Uvođenjem dušikovog atoma u aglikonski prsten otkrivena je nova grupa 15-članih makrolidnih antibiotika − azalidi. Azalidi pokazuju povećanu metaboličku stabilnost, izuzetnu farmakokinetiku i širok spektar antibakterijske aktivnosti. Prvi i zasad jedini azalidni makrolidni lijek na tržištu je azitromicin. Nezavisno od antibakterijske aktivnosti, makrolidi također pokazuju i protuupalnu aktivnost. Izoksazol je peteročlani heterociklički spoj koji pokazuje različita farmakološka djelovanja te je zbog toga važan intermedijer za sintezu novih spojeva u medicinskoj kemiji. Izoksazolni prsten može se koristiti za razvoj novih spojeva s različitim biološkim djelovanjem poput antimikrobnog, antivirusnog, antikancerogenog, protuupalnog, imunomodulatornog, antikonvulzivnog ili antidijabetičkog. Cilj ovog diplomskog rada je priprava novih azalidnih spojeva u kojima je makrociklički laktonski prsten povezan s izoksazolom. Novosintetiziranim spojevima ispitat će se antiinfektivno djelovanje određivanjem minimalne inhibicijske koncentracije (MIC) na različitim sojevima Gram-pozitivnih i Gram-negativnih bakterija.

Abstract (english)

Macrolides represent a large group of compounds with antibacterial activity. They are characterized by a highly substituted macrolactone ring, an aglycone, to which are attached one or more neutral or amino sugars via a glycosidic bond. By introducing a nitrogen atom into the aglycone ring, a new group of 15-membered macrolide antibiotics − azalides, was discovered. Azalides show increased metabolic stability, exceptional pharmacokinetics and antibacterial spectrum. The first and so far the only azalide macrolide on the market is azithromycin. Macrolides also possess anti-inflammatory properties, independent of their antibiotic actions. Isoxazole is a five-membered heterocyclic compound having various pharmacological action, and because of that is an important intermediate for the synthesis of new chemicals in medicinal chemistry. Isoxazole scaffold can be used to develop new agents with various biological activities (e.g. antimicrobial, antiviral, anticancer, antiinflammatory, immunomodulatory, anticonvulsant or antidiabetic properties). The aim of this thesis is to prepare new hybrid molecules of azalides and isoxazole. Minimum inhibitory concentration (MIC) of synthesized compounds will be determined against Gram-positive and
Gram-negative bacterial strains.

• Keywords: azalidi; izoksazol; antibakterijsko djelovanje
• Keywords (english): azalides; isoxazole; antibacterial activity
• Language: croatian
• URN:NBN: urn:nbn:hr:149:094890
• Study programme: Title: Applied Chemistry - Graduate study; specializations in: Environmental chemistry and green technologies, Advanced materials and technologies, Applied organic chemistry; Course: Applied organic chemistry; Study programme type: university; Study level: graduate; Academic / professional title: sveučilišni/a magistar/magistra primijenjene kemije (sveučilišni/a magistar/magistra primijenjene kemije)
• Type of resource: Text
• File origin: Born digital
• Access conditions: Embargoed access; Embargo expiration date: 2025-10-01
• Created on: 2023-11-24 09:41:39