Sinteza novih aril-supstituiranih 1,2,3-triazolnih derivata purina i purinskih bioizostera

undergraduate thesis

• Title (english): The synthesis of new aryl-substituted 1,2,3-triazole purine and purine bioisosteres
• Author: Elizabeta Forjan
• 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 ovog rada bila je sinteza novih aril-supstituiranih 1,2,3-triazolnih derivata purina i purinskih bioizostera 7–11, kao racemične smjese, s potencijalnim antitumorskim djelovanjem. U tu svrhu sintetizirani su propargilirani derivati indola, benzimidazola, 6-klor-9H-purina, 4-klor-7H-pirolo[2,3-d]pirimidina i 4-klor-1H-imidazo[4,5-c]piridina 1–5 te odgovarajući aromatski 1,2-azidoalkohol. Reakcijama 1,3-dipolarne cikloadicije odgovarajućeg azida 6 i terminalnih alkina 1 ̶ 5 uz Cu(I) kao katalizator, koje su provedene primjenom ultrazvuka, dobiveno je pet novih konjugata purina i purinskih bioizostera 7–11. Strukture svih sintetiziranih spojeva potvrđene su 1H NMR i 13C NMR spektroskopijom.

Abstract (english)

The aim of this work was the synthesis of new aryl-substituted 1,2,3-triazole purine and purine bioisosteres 7–11, as racemic mixture, with potential antitumor activity. For this purpose, propargylated indole, benzimidazole, 6-chloro-9H-purine, 4-chloro-1H-imidazo[4,5-c]pyridine and 4-chloro-7H-pyrrolo[2,3-d]pyrimidine were synthesised. Furthermore, para-bromo substituted phenacyl bromides were treated with NaN3, followed by fast reduction with NaBH4 to afford corresponding azido alcohol with secondary hydroxyl group. Triazole derivatives of purine and purine bioisosteres were then prepared using 1,3-dipolar cycloaddition of the corresponding azide 6 and terminal alkynes 1–5 with Cu(I) as catalyst using ultrasound irradiation. The structures of all synthesised compounds were confirmed by 1H NMR and 13C NMR spectroscopy.

• Keywords: purin; purinski bioizosteri; „klik“ kemija; alkin-azid cikloadicija; ultrazvučna sinteza
• Keywords (english): purine; purine bioisosteres; “click” chemistry; alkyne-azide cycloaddition; sonochemistry
• Language: croatian
• URN:NBN: urn:nbn:hr:149:915212
• 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: 2023-03-28 07:48:39