N-Sübstitüe amidin grubu taşıyan bazı heterosiklik halkaların sentez, yapı-aydınlatmaları ve antimikrobial etkileri üzerinde çalışmalar
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2001
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Sağlık Bilimleri Enstitüsü
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76 SUMMARY Studies on the Synthesis, Structure Elucidation of Some N-Substituted Heterocyclic Rings Having Carboxamidine Group and Evaluation of Their Antimicrobial Activities In this study, 5 new targeted of N-sübstituted-2-(sübstituted-phenyl)-lH- benzimidazole-5(6)-carboxamidine (3a-3e) were prepared by using Pinner reaction. First, 4-amino-3-nitrobenzonitrile was reduced to 3,4-diaminobenzo- nitrile (1) with H2, Pd / C in Parr apparatus. Then, the reaction of 1 with the sodiummetabisulfite adduct of appropriate aldehydes in dimethylformamide realised benzimidazole cyclization (2a-c). Nitril group of these compounds were converted to imidate ester by using anhydrous ethanol and hydrogen chloride gas which was dried over sulphiric acid. Then these unstable esters were immediately transform into to the requested 5(6)-carboxamidine benzimidazole derivatives (3a-3e). In this study, 5 new targeted compounds as well as 3 intermediates were prepared for the first time by the given reactions above. The purity of the synthesized compounds were controlled by thin layer chromatography and melting points were determined and uncorrected. The chemical structure of the compounds were elucidated by their Infrared, Nuclear Magnetic Rezonans, Mass spectral data and their elemental analysis results. The in vitro antifungal activity of the synthesized compounds against Candida albicans were evaluated by the Disc Diffusion Techniques. Among them compound 3c, showed close activity with 21 mm inhibition zone to the reference compound Miconazole. Key Words : Amidine Derivatives, Benzimidazole Nitril Derivatives, lH-Benzimidazole Carboxamidine Derivatives, Synthesis and Structure Elucidation, Antifungal Activity.
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