Novi derivati 2-arilbenzimidazola: sinteza i strukturna karakterizacija

undergraduate thesis

• Title (english): The novel 2-arylbenzimidazole derivatives: synthesis and structural characterization
• Author: Viktorija Maričić
• Mentor: Tatjana Gazivoda Kraljević (mentor)
• Committee member: Tatjana Gazivoda Kraljević (predsjednik povjerenstva)
• Committee member: Dragana Vuk (član povjerenstva)
• Committee member: Dajana Kučić Grgić (član povjerenstva)
• Granter: University of Zagreb; Faculty of Chemical Engineering and Technology; Zagreb
• Defense date and country: 2023-09-22, Croatia
• Scientific / art field, discipline and subdiscipline: NATURAL SCIENCES; Chemistry

Abstract

Ovaj rad opisuje sintezu novih derivata benzimidazola (8–15) premoštenih 1,2,3-triazolom. Novopripravljeni spojevi su strukturno okarakterizirani 1H- i 13C-NMR spektroskopijom te su analizom in silico (PASS) predviđena njihova vjerojatna farmakološka djelovanja i biološke mete. Reakcijom kondenzacije 4-klorbenzen-1,2-diamina s etil-kloracetatom sintetiziran je 6-klor-2-klormetilbenzimidazol (1). 6-klor-2-klormetilbenzimidazol (1) i 2-klormetilbenzimidazol su potom prevedeni u azidne derivate (2 i 3) potrebne za klik reakciju. Derivati benzensulfamida s terminalnom alkinskom skupinom (4–7) sintetizirani su reakcijom propargiliranja. Huisgenovom 1,3-dipolarnom cikloadicijom azidometilnih derivata (2 i 3) s odgovarajućim alkinilnim benzensulfamidima (4–7) u prisustvu Cu(OAc)2 kao katalizatora sintetizirani su 1,4-disupstituirani 1,2,3-triazolni derivati benzimidazola 8–15.

Abstract (english)

This paper describes synthesis of novel benzimidazole derivatives (8– 15) linked by
1,2,3-triazole. The newly prepared compounds were structurally characterized by 1H- and 13C-NMR spectroscopy, and their probable biological activities were predicted by in silico analysis (PASS). 6-chloro-2-chloromethylbenzimidazole (1) was synthesized by the condensation reaction of 4-chlorobenzene-1,2-diamine with ethyl chloroacetate.
6-chloro-2-chloromethylbenzimidazole (1) and 2-chloromethylbenzimidazole were then converted into azide derivatives (2 and 3) required for the click reaction. Derivatives of benzenesulfamide with a terminal alkyne group (4–7) were synthesized by the propargylation reaction. The 1,4-disubstituted 1,2,3-triazole benzimidazole derivatives (8–15) were synthesized by Huysgen 1,3-dipolar cycloaddition of azidomethyl derivatives (2 and 3) with corresponding alkynyl benzenesulfamides (4–7) in the presence of Cu(OAc)2 as a catalyst.

• Keywords: benzimidazol; 1 2 3-triazol; klik kemija
• Keywords (english): benzimidazole; 1 2 3-triazole; click chemistry
• Language: croatian
• URN:NBN: urn:nbn:hr:149:940448
• 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: Embargoed access; Embargo expiration date: 2025-10-01
• Created on: 2023-11-30 12:40:25