Priprava i karakterizacija 2-feniletil-, 3-piridil-, dimetil-izoksazol-4-il, 4-piperidilsulfonilfenil-i tetrahidro-3-furfuril-makrozona, novih konjugata makrolidnih antibiotika

master's thesis

• Title (english): Preparation and characterization of a 2-phenylethyl-, 3-pyridyl-, 3,5-dimethylisoxazol-4-yl, 4-piperidylsulfonylphenyl- and tetrahydro-3-furfuryl-macrozone, new conjugates of macrolide antibiotics
• Author: Ana-Marija Lulić
• Mentor: Predrag Novak (mentor)
• Committee member: Predrag Novak (predsjednik povjerenstva)
• Committee member: Vesna Petrović Peroković (član povjerenstva)
• Committee member: Željka Soldin (član povjerenstva)
• Committee member: Sanda Rončević (član povjerenstva)
• Granter: University of Zagreb; Faculty of Science; (Department of Chemistry); Zagreb
• Defense date and country: 2020-02-27, Croatia
• Scientific / art field, discipline and subdiscipline: NATURAL SCIENCES; Chemistry

Abstract

Makrolidi su velika klasa antibiotika koje karakterizira širok spektar antibakterijskog djelovanja i slična kemijska struktura. Građeni su od makrolaktonskog prstena na koji mogu biti vezane šećerne jedinice, najčešće desozamin i kladinoza. Zbog pretjerane upotrebe antibiotika u medicini, veterinarstvu i uzgoju biljaka, bakterije su razvile mehanizme otpornosti, a potencijalno rješenje ovog problema je sinteza i dizajn novih makrolida kemijskom modifikacijom već postojećih. Makrozoni su nova klasa derivata makrolidnih antibiotika u kojima je na poziciju 9a makrolaktonskog prstena vezana molekula tiosemikarbazona preko molekule poveznice. Sintetizirani su 2-feniletil-, 3-piridil-, 3,5-dimetilizoksazol-4-il-, 4-piperidilsulfonilfenil- i tetrahidro-3-furfuril-makrozon u tri reakcijska koraka. Dobiveni makrozoni pročišćeni su kromatografijom na koloni, a zatim su strukturno karakterizirani jednod- i dvodimenzijskom spektroskopijom NMR.

Abstract (english)

Macrolides are a large class of antibiotics known for a wide range of antibacterial activity and similar chemical structure. Their structure is made up of a macrolactone ring to which sugar units may be attached, most commonly desosaminosis and cladinosis. Due to the overuse of antibiotics in medicine, veterinary medicine and cultivation of plants, bacteria have developed resistance mechanisms. Potential solution to this problem is the synthesis and design of new macrolides by chemical modification of existing ones. Macrozones are a new class of macrolide antibiotic derivatives in which a thiosemicarbazone molecule is attached to the position 9a of the macrolactone ring via linkage molecule. 2-phenylethyl-, 3-pyridyl-, 3,5-dimethylisoxazol-4-yl-, 4-piperidylsulfonylphenyl- and tetrahydro-3-furfuryl-macrozone were synthesized in three reaction steps. The resulting macrozones were purified by column chromatography and structurally characterized by one and two-dimensional NMR spectroscopy.

• Keywords: azitromicin; kromatografija; makrolidi; spektroskopija NMR; tiosemikarbazoni
• Keywords (english): azithromicyn; chromatography; macrozones; NMR; thiosemicarbazones
• Language: croatian
• URN:NBN: urn:nbn:hr:217:954724
• Study programme: Title: 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 resource: Text
• File origin: Born digital
• Access conditions: Open access
• Created on: 2020-09-07 12:33:26