Synthesis and chemical modification of 2-(3-nitrobenzylidene) amino-1H-benzimidazole derivatives and their antibacterial activity : diploma thesis

2-Amino-1H-benzimidazol zahvaljući svom širokom spektru biološke aktivnosti prema različitim oboljenjima, dio je strukture velikog broja lijekova (Bezitramid, Dibazol, Mebendazol…). Iako je nekoliko metoda sinteze 2-amino-1H- benzimidazola već poznato, pronalazak novih metoda sinteze bio bi od velike važnosti za otkriće novih lijekova. Obzirom da je navedeni spoj potencijalno dobar kemoterapeutik, zanimljiv je i za organsku i medicinsku kemiju. Kondezacijom Schiffove baze s odabranim sekundarnim i primarnim aminima, nitrilima i diketonima, koji u svojoj strukturi sadrže aktivne metilenske skupine, dobiveni su različiti derivati spoja 2-(3-nitrobenziliden)amino-1H-benzimidazola. U svrhu praćenja sinteze korištena je tankoslojna kromatografija (TLC). Sintetizirani spojevi potvrđeni su 1 H NMR i IR spektroskopijom kao i elementnom analizom. Svi dobiveni spojevi podvrgnuti su daljnjim ispitivanjima antibakterijske aktivnosti na Gram-pozitivni bakterijski soj (Staphylococcus aureus) i Gram-negativne bakterijske sojeve (Escherichia coli i Pseudomonas aeruginosa). Dobiveni rezultati bioloških testova omogućit će određivanje odnosa između strukture i biološke aktivnosti (SAR).2-Amino-1H-benzimidazole thanks to its wide range of biological activity against various illnesses is part of the structure of a large number of drugs (Bezitramid, Dibazol, Mebendazol ...). Although several methods of synthesis of 2-amino- 1H-benzimidazole are already known, finding of new synthetic methods would be of great importance for the discovery of new drugs. Considering that mentioned compound has potentially good chemotherapeutic characteristics, it is interesting to organic and medical chemistry. By condensing the Schiff base with the selected secondary and primary amines, nitriles and diketones, which contain active methylene groups in its structure, various derivatives of 2- (3-nitrobenzylidene) amino-1H-benzimidazole are obtained. Thin layer chromatography (TLC) was used to monitor the synthesis. The synthesized compounds were confirmed by 1 H NMR and IR spectroscopy as well as elemental analysis. All the obtained compounds are tested for the antibacterial activity on Gram positive bacterial strain (Staphylococcus aureus) and Gram negative bacterial strains (Escherichia coli i Pseudomonas aeruginosa). The obtained biological test results will allow the determination of the relationship between structure and biological activity (SAR)