Sinteza hibrida purina, pseudopurina i L-askorbinske kiseline s 1,2,3-triazolnom premosnicom

undergraduate thesis

• Title (english): Synthesis of purine, pseudopurine and L-ascorbic acid hybrids with a 1,2,3-triazole linker
• Author: Helena Prpić
• Mentor: Silvana Raić-Malić (mentor)
• Committee member: Silvana Raić-Malić (predsjednik povjerenstva)
• Committee member: Andrijana Meščić Macan (član povjerenstva)
• Committee member: Šime Ukić (član povjerenstva)
• Granter: University of Zagreb; Faculty of Chemical Engineering and Technology; Zagreb
• Defense date and country: 2017-07-14, Croatia
• Scientific / art field, discipline and subdiscipline: NATURAL SCIENCES; Chemistry; Organic Chemistry

Abstract

Cilj ovog rada bila je sinteza novih potencijalno biološki aktivnih hibrida purinskih izostera i L-askorbinske kiseline (15 – 19) povezanih preko 1,2,3-triazolne poveznice. U tu svrhu priređeni su N-propargilni purinski i pseudopurinski derivati (6 – 10), te 6-azido-2,3-O,O-dibenzil-L-askorbinska kiselina (14) višestupnjevitom sintezom. 1,4-disupstituirana 1,2,3-triazolna premosnice pripravljena je Cu(I) kataliziranom regioselektivnom 1,3-dipolarnom cikloadicijom 6-azido derivata L-askorbinske kiseline (14) i odgovarajućih terminalnih alkina purinskih izostera (6 – 10). Ciljani hibridi (15 – 19) pripravljeni su „click“ reakcijom potpomognutom ultrazvučnim (metoda A) i mikrovalnim (metoda B) zračenjem koristeći CuSO4 i Cu(0), kao izvor Cu(I) iona, te klasičnom sintezom primjenom Cu(OAc)2 u metanolu na sobnoj temperaturi (metoda C). Strukture svih priređenih spojeva potvrđene su 1H NMR, 13C NMR i MS spektroskopijom.

Abstract (english)

The aim of this work was the synthesis of novel biologically active of purines, pseudopurines and L-ascorbic acid hybrids (15 – 19) connected through 1,2,3-triazole linker. For this purpose, N-propargylated purine and pseudopurine derivatives (6 – 10) and 6-azido-2,3-O,O-dibenzyl-L-ascorbic acid (14) were prepared in a multistep syntheses. The 1,4-disubstituted 1,2,3-triazole spacer was synthesized using Cu(I)-catalyzed regioselective 1,3-dipolar cycloaddition reaction of 6-azido-L-ascorbic acid derivative (14) with the corresponding purine isostere terminal alkynes (6 – 10). The target hybrids (15 – 19) were prepared by ultrasound (method A) and microwave (method B) assisted “click” reactions using CuSO4 and Cu(0), as catalysts, as well as using classical synthetic protocol with Cu(OAc)2 in methanol (method C). The structures of all synthesized compounds were confirmed by 1H NMR, 13C NMR and MS spectroscopy.

• Keywords: molekulski hibridi; L-askorbinska kiselina; purinski izosteri; Huisgenova 1 3-dipolarna cikloadicija; ultrazvučno i mikrovalno potpomognute reakcije
• Keywords (english): molecular hybrids; L-ascorbic acid; purine isosteres; Huisgen 1 3-dipolar cycloaddition; ultrasound and microwave assisted reactions
• Language: croatian
• URN:NBN: urn:nbn:hr:149:171898
• Study programme: Title: Applied Chemistry - Undergraduate 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: undergraduate; Academic / professional title: sveučilišni/a prvostupnik/prvostupnica (baccalaureus/baccalaurea) primijenjene kemije (sveučilišni/a prvostupnik/prvostupnica (baccalaureus/baccalaurea) primijenjene kemije)
• Type of resource: Text
• File origin: Born digital
• Access conditions: Open access
• Created on: 2021-01-08 11:19:53