Novi amidino supstituirani konjugati benzimidazola kao potencijalni antitumorski agensi

master's thesis

• Title (english): Novel amidino substituted benzimidazole conjugates as potential antitumor agents
• Author: Emina Mehić
• Mentor: Marijana Hranjec (mentor)
• Committee member: Marijana Hranjec (predsjednik povjerenstva)
• Committee member: Maja Cindrić (član povjerenstva)
• Committee member: Jasna Prlić Kardum (član povjerenstva)
• Granter: University of Zagreb; Faculty of Chemical Engineering and Technology; Zagreb
• Defense date and country: 2018-07-12, Croatia
• Scientific / art field, discipline and subdiscipline: NATURAL SCIENCES; Chemistry; Organic Chemistry

Abstract

U okviru ovog rada provedena je sinteza i spektroskopska karakterizacija novih amidino supstituiranih derivata benzimidazola 17˗28, 5-cijano-N-supstituiranih 38˗41 i N-supstituiranih 55˗58 2-aminobenzimidazola te Schiffovih baza benzimidazola 42˗47. Ciljani spojevi pripravljeni su klasičnim reakcijama organske sinteze te mikrovalovima potpomognutom sintezom. Amidino supstituirani 1,2-fenilendiamini 10˗13 kao glavni prekursori za sintezu amidino supstituiranih derivata benzimidazola 17˗28, priređeni su iz 4-amino-3-nitrobenzonitrila 4 Pinnerovom reakcijom u kiselom mediju. Ciljani spojevi 17˗28 sintetizirani su kondenzacijom priređenih prekursora 10˗13 s odgovarajućim aromatskim aldehidima 14˗15 uz korištenje p-benzokinona kao oksidansa. 5-cijano-N-supstituirani derivati 38-41 te N-supstituirani derivati 55-58 benzimidazola priređeni su u nekoliko sintetskih koraka iz 4-klor-3-nitrobenzonitrila 29, odnosno 2-klor-nitrobenzena 48. 4-klor-3-nitrobenzonitril 29 i 2-klor-nitrobenzen 48 podvrgnuti su nekatalitičkoj aminaciji potpomognutoj mikrovalnim zračenjem sa suviškom amina. Nakon redukcije nitro derivata, u reakciji s BrCN priređeni su odgovarajući 2-aminobenzimidazoli. Priređeni 5-cijano-N-supstituirani derivati benzimidazola 38-41 u reakciji s odgovarajućim aldehidima 14-15 daju Schiffove baze benzimidazola 42-47. Strukture svih priređenih produkata potvrđene su 1H i 13C NMR spektroskopijom te masenom spektrometrijom. Tijek Pinnerovih reakcija kod priprave amidino supstituiranih prekursora praćen je IR spektroskopijom.

Abstract (english)

This work presents the synthesis and spectroscopic caracterization of novel amidino substituited benzimidazoles 17-28, 5-cyano-N-substituited 38-41 and N-substituited 55-58 2-aminobenzimidazoles and benzimidazole derived Schiff's bases of 42-47. Target compounds were prepared by conventional reactions of organic syntheses as well as by microwave assisted reactions. Amidino substituited 1,2-phenylenediamines 10-13 as the main precursors for the synthesis of targeted amidino substituited benzimidazoles 17-28 were prepared starting from 4-amino-3-nitrobenzonitrile 4 by Pinner reaction. Target compounds 17-28 were synthesized by condensation of the prepared precursors 10-13 with the corresponding aromatic aldehydes 14-15 using p-beznoquinone as an oxidant. 5-cyano-N-substituited derivatives 38-41 and N-substituited derivates 55-58 of benzimidazole were prepared in several synthetic steps from 4-chloro-3-nitrobenzonitrile 29 or 2-chloronitrobenzene 48. 4-chloro-3-nitrobenzonitrile 29 and 2-chloronitrobenzene 48 were exposed to non-catalytic amination microwave assisted reaction with an excessive amount of amine. After reduction of nitro derivates, corresponding 2-aminobenzimidazoles were prepared in reaction with BrCN. Prepared 5-cyano-N-substituited benzimidazole derivates 38-41 in reaction with corresponding aldehydes 14-15 gives the Schiff base of benzimidazole 47˗47. The structures of all prepared products were confirmed by 1H and 13C NMR spectroscopy and mass spectrometry. The Pinner reaction in the preparation of amidino substituited precursors was monitored by IR spectroscopy.

• Keywords: benzimidazoli; amidini; Schiffove baze; 1H i 13C NMR spektroskopija; masena spektrometrija
• Keywords (english): benzimidazoles; amidines; Schiff's base; 1H and 13C NMR spectroscopy; mass spectrometry
• Language: croatian
• URN:NBN: urn:nbn:hr:149:071480
• Study programme: Title: Chemical Engineering - Graduate study; Study programme type: university; Study level: graduate; Academic / professional title: magistar/magistra inženjer/inženjerka kemijskog inženjerstva (magistar/magistra inženjer/inženjerka kemijskog inženjerstva)
• Type of resource: Text
• File origin: Born digital
• Access conditions: Open access
• Created on: 2020-06-02 12:25:19