Sinteza novih aril-supstituiranih N-heterocikla sa sekundarnom hidroksilnom skupinom

undergraduate thesis

• Title (english): Synthesis of new aryl-substituted N-heterocycles with hydroxyl group
• Author: Doria Curiš
• Mentor: Silvana Raić-Malić (mentor)
• Committee member: Silvana Raić-Malić (predsjednik povjerenstva)
• Committee member: Silvija Maračić (član povjerenstva)
• Committee member: Danijela Ašperger (član povjerenstva)
• Granter: University of Zagreb; Faculty of Chemical Engineering and Technology; Zagreb
• Defense date and country: 2021-09-15, Croatia
• Scientific / art field, discipline and subdiscipline: NATURAL SCIENCES; Chemistry

Abstract

Cilj ovoga rada je regioselektivna sinteza novih aril-supstituiranih N-heterocikličkih 1,2,3-triazolnih derivata 7–11 s potencijalnom antitumorskom aktivnošću. U tu su svrhu reakcijom N-propargiliranja sintetizirani terminalni alkini indola, benzimidazola, 4-klor-7H-pirolo[2,3-d]pirimidina, 6-klorpurina i 4-klor-1H-imidazo[4,5-c]piridina 1–5. Nukleofilnom supstitucijom 2-brom-4-kloracetofenona s natrijevim azidom, a potom redukcijom primjenom natrijevog borovog hidrida, priređen je odgovarajući azidni derivat 6. Novi 1,2,3-triazolni derivati 7–11 pripravljeni su, kao racemične smjese, reakcijom 1,3-dipolarne cikoladicije različitih N-propargiliranih alkina 1–5 i odgovarajućeg azida 6 uz Cu(I), kao katalizator, prema načelima "klik" kemije. Strukture spojeva potvrđene su spektroskopijom 1H i 13C NMR, a biološka ispitivanja novopriređenih konjugata 7–11 su u tijeku.

Abstract (english)

The aim of this work was the regioselective synthesis of novel conjugates of purine and purine bioisosteres 7–11 with potential antitumor activity. For this purpose, various terminal alkynes were synthesized using N-propargylation reaction of indole, benzimidazole, 4-chloro-7H-pyrolo[2,3-d]pyrimidine, 6-chloropurine and 4-chloro-1H-imidazo[4,5-c]pyridine 1–5. The corresponding azide derivative was synthesized by nucleophilic substitution of 2-bromo-4-chloroacetophenone with sodium azide, followed by reduction using sodium borohydride. 1,2,3-triazole derivatives 7–11 were prepared, as racemic mixture, using 1,3-dipolar cycloaddition reaction of the various N-propargylated alkynes 1–5 and corresponding azide 6 with Cu(I), as a catalyst, following the concept of "click" chemistry. The structures of compounds have been confirmed by 1H and 13C NMR spectroscopy and the biological evaluations novel conjugates 7–11 are in progress.

• Keywords: "klik" kemija; bakrom katalizirana 1 3-dipolarna cikloadicija; 1 2 3-triazol; "zelena" kemija
• Keywords (english): "click" chemistry; copper(I) catalyzed 1 3-dipolar cycloaddition; 1 2 3-triazole; "green" chemistry
• Language: croatian
• URN:NBN: urn:nbn:hr:149:987207
• Project: Number: IP-2018-01-4682; Title: Novi spojevi temeljeni na bioizosterima purina za ispitivanje njihovih antitumorskih i antipatogenih djelovanja; Acronym: PurBioCaPa; Leader: Silvana Raić-Malić; Jurisdiction: Croatia; Funder: HRZZ; Funding stream: IP
• Study programme: Title: Materials Science and Engineering - Undergraduate study; Study programme type: university; Study level: undergraduate; Academic / professional title: sveučilišni/a prvostupnik/ prvostupnica (baccalaureus/baccalaurea) inženjer/inženjerka kemijskog inženjerstva (sveučilišni/a prvostupnik/ prvostupnica (baccalaureus/baccalaurea) inženjer/inženjerka kemijskog inženjerstva)
• Type of resource: Text
• File origin: Born digital
• Access conditions: Open access; Embargo expiration date: 2022-09-01
• Created on: 2023-03-24 11:39:21