Sinteza novih bioizostera purina s potencijalnim antipatogenim djelovanjem

master's thesis

• Title (english): Synthesis of purine bioisosteres with potential antipathogenic activity
• Author: Helena Prpić
• Mentor: Silvana Raić-Malić (mentor)
• Committee member: Silvana Raić-Malić (predsjednik povjerenstva)
• Committee member: Silvija Maračić (član povjerenstva)
• Committee member: Šime Ukić (član povjerenstva)
• Granter: University of Zagreb; Faculty of Chemical Engineering and Technology; Zagreb
• Defense date and country: 2019-09-20, Croatia
• Scientific / art field, discipline and subdiscipline: NATURAL SCIENCES; Chemistry

Abstract

Cilj ovog rada bila je sinteza novih potencijalno biološki aktivnih benztiazolnih (21-29, 33-35) i benzimidazolnih (36-47) derivata kao bioizostera purina. U tu svrhu pripravljeni su 2-(4-hidroksi-3-metoksifenil)benztiazolni derivati (18-20) koji su zatim O-alkiliranjem, prevedeni u 2-(4-alkoksi-3-metoksifenil)benztiazolne derivate (21-29). Propargiliranjem 2-(4-hidroksi-3-metoksifenil)benztiazolnih derivata (18-20) priređeni su O-propargilirani derivati benztiazola (30-32). Bakar kataliziranom Huisgenovom 1,3-dipolarnom cikloadicijom terminalnih alkina i etilmorfolinskog azida (16) priređeni su 1,2,3-triazolni derivati benztiazola (33-35). Reakcijom odgovarajućih haloalkilirajućih reagensa (9, 10, 12 ili 17) s o-fenildiaminima sintetizirani su 2-(4-alkoksi-3-metoksifenil)benzimidazolni derivati (39-47), dok 2-(4-alkoksi-3-metoksifenil)benzimidazolni derivati (36-38) nisu uspješno sintetizirani. Ciljani benzimidazolni derivati dobiveni su reakcijama potpomognutima mikrovalnim zračenjem u metanolu. Strukture svih priređenih spojeva potvrđene su 1H NMR i 13C NMR spektroskopijom.

Abstract (english)

The aim of this work was the synthesis of novel biologically active benzothiazole (21-29) and benzimidazole (36-47) derivatives as purine bioisosteres. For this purpose, 2-(4-hydroxy-3-methoxyphenyl) benzothiazole derivatives (18-20) were prepared, which were then converted to 2-(4-alkoxy-3-methoxyphenyl) benzothiazole derivatives (21-29) by O-akylation. O-Propargylated benzothiazole derivatives (30-32) were prepared by propargylation of 2-(4-hydroxy-3-methoxyphenyl) benzothiazole derivatives (18-20). Copper-catalyzed Huisgen 1,3-dipolar cycloaddition of terminal alkynes and ethylmorpholine azide (16) afforded 1,2,3-triazole benzothiazole derivatives (33-35) By reaction of corresponding haloalkylating reagents (9, 10, 12 or 17) with o-phenyldiamines, 2-(4-alkoxy-3-methoxyphenyl) benzimidazole derivatives (39-47) were synthesized, while 2-(4-Alkoxy-3-methoxyphenyl) benzimidazole derivatives (36-38) have not been successfully synthesized. Targeted benzimidazole derivatives were obtained under microwave irradiation in methanol. The structures of all newly prepared compounds were confirmed by 1H and 13C-NMR spectroscopy.

• Keywords: benztiazol; benzimidazol; 1 2 3- triazol; klik reakcija; Huisgenova 1 3-dipolarna cikloadicija; mikrovalno potpomognute reakcije
• Keywords (english): benzothiazole; benzimidazole; 1 2 3- triazole; click reaction; Huisgen 1 3-dipolar cycloaddition; microwave assisted reaction
• Language: croatian
• URN:NBN: urn:nbn:hr:149:345997
• 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: 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: Access restricted to students and staff of home institution
• Created on: 2022-02-27 11:18:07