Novi 1,2,3-triazolni derivati kumarina: sinteza Pd-kataliziranim i "klik" reakcijama, spektroskopska svojstva i antitumorska aktivnost

master's thesis

• Title (english): The novel coumarin derivatives: synthesis using Pd-catalysed and "click" reactions, spectroscopic properties and antitumor activity
• Author: Mia Krnić
• Mentor: Tatjana Gazivoda Kraljević (mentor)
• Committee member: Tatjana Gazivoda Kraljević (predsjednik povjerenstva)
• Committee member: Silvana Raić-Malić (član povjerenstva)
• Committee member: Lidija Furač (član povjerenstva)
• Granter: University of Zagreb; Faculty of Chemical Engineering and Technology; Zagreb
• Defense date and country: 2016-07-12, Croatia
• Scientific / art field, discipline and subdiscipline: NATURAL SCIENCES; Chemistry; Organic Chemistry

Abstract

U ovom je radu prikazana sinteza, spektroskopska karakterizacija i in silico analiza C-3 supstituiranih 1,2,3-triazolnih i alkinilnih derivata kumarina (3-22). Početni spoj za „klik“ reakcije, 3-azido-7-hidroksikumarin (2) pripravljen je Perkinovom reakcijom. U položaj C-3 kumarinskog prstena uvedeni su 1,2,3-triazolni supstituenti mikrovalovima potpomognutim „klik“ reakcijama s odgovarajućim terminalnim alkinima uz Cu katalizator pri čemu su sintetizirani spojevi (3-20). Sonogashira-inom reakcijom unakrsnog povezivanja 7-hidroksi-3-klor-4-metilkumarina s odgovarajućim arilnim terminalnim alkinima uz katalizator Pd(PPh3)4 i CuI kao kokatalizator pripravljeni su 3-ariletinil-7-hidroksi-4-metil kumarini 21 i 22. „One-pot“ reakcijom 7-hidroksi-3-klor-4-metilkumarina, NaN3, L-prolina i NaOH nije sintetiziran 3-azido-7-hidroksi-4-metilkumarin koji je trebao poslužiti kao početni spoj za „klik“ reakcije. Strukturna i spektroskopska karakterizacija spojeva provedena je 1H NMR, UV/Vis i fluorimetrijskom spektroskopijom. In silico analizom (PASS) predviđene su farmakološke aktivnosti i moguće biološke mete novopripravljenih spojeva.

Abstract (english)

This paper describes synthesis, spectroscopic characterization and in silico analysis of C-3 substituted 1,2,3-triazole and alkynyl coumarin derivatives (3-22). Starting compound for „click“ reactions, 3-azido-7-hydroxycoumarin (2) was prepared by Perkin reaction. In position C-3 of coumarin ring were introduced 1,2,3-triazole substituents with Cu-catalyzed „click“ reactions under microvawe irradiation with corresponding terminal alkynes whereby compounds (3-20) were synthesized. Compounds of 3-arylethynyl-7-hydroxy-4-methylcoumarin (21-22) were prepared by Sonogashira cross-coupling reaction with corresponding aryl terminal alkynes, catalyst Pd(PPh3)4 and cocatalyst CuI. „One-pot“ reaction with mixture of 7-hydroxy-3-chlor-4-methylcoumarin, NaN3, L-prolin and NaOH was not successful for synthesis starting compound for „click“ reactions, 3-azido-7-hydroxy-4-methylcoumarin. Structural and spectroscopic characterization of 1,2,3-triazole coumarin derivatives was conducted using 1H-NMR, UV/Vis and fluorescence spectroscopy. Pharmacological effects and possible biological targets for novel synthesized compounds were provided using in silico analysis (PASS).

• Keywords: derivati 7-hidroksikumarina; 1 2 3-triazol; "klik“ reakcija; Sonogashira-ina reakcija unakrsnog povezivanja; Perkinova reakcija
• Keywords (english): 7-hydroxycoumarin derivatives; 1 2 3-triazole; "click" reaction; Sonogashira cross-coupling reaction; Perkin reaction
• Language: croatian
• URN:NBN: urn:nbn:hr:149:426693
• Study programme: Title: Applied Chemistry - Graduate 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: graduate; Academic / professional title: magistar/magistra primijenjene kemije (magistar/magistra primijenjene kemije)
• Type of resource: Text
• File origin: Born digital
• Access conditions: Open access
• Created on: 2017-04-25 09:02:06