Sinteza novih aril-supstituiranih 1,2,3-triazolnih derivata purina i purinskih bioizostera
Autor: | Forjan, Elizabeta |
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Přispěvatelé: | Raić-Malić, Silvana |
Jazyk: | chorvatština |
Rok vydání: | 2021 |
Předmět: |
purine
purinski bioizosteri „klik“ kemija alkyne-azide cycloaddition „zelena“ kemija eutektička otapala mehanokemijska sinteza ferocen bioizosteri purina bioizosteri pirimidina 1 2 3-triazoli Huisgenova 1 3-dipolarna cikloadicija alkin-azid cikloadicija purin purine bioisosteres ultrazvučna sinteza PRIRODNE ZNANOSTI. Kemija NATURAL SCIENCES. Chemistry sonochemistry “click” chemistry |
Popis: | 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. 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. |
Databáze: | OpenAIRE |
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