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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. 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. |
