Synthesis, derivatization, characterization and anti-microbial screening of Azo compounds.

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MAY, 2016
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Abstract
In our research group, two azo dyes were recently demonstrated to have antimicrobial activity. Structural modification of these compounds resulted in seven novel dyes. Five compounds were synthesised by the two-step diazotization-coupling reaction sequence. Employing the Williamson’s synthesis and acetylation with acetic anhydride, the ether and acetyl derivatives were synthesised respectively. The synthesised dyes, with good yields, have been characterised with IR, Mass Spec. and 1H NMR, and the melting point as well as retardation factor determined. The Broth Dilution method was used in determining the antimicrobial activity against the organisms, Staphylococcus aureus, Streptococcus pyrogenes, Salmonella typhi, Pseudomonas aeruginosa and Candida albicans. The synthesised compounds showed a broad spectrum of activity, with greater gram-negative and antifungal activity. The alkylated products, (E)-1-(4-ethoxynaphthalen-1-yl)-2-(4-nitrophenyl)diazene (KA 008), (E)-4-((4-ethoxynaphthalen-1-yl)diazenyl benzoic acid (KA 009) were the most active of all the compounds synthesised, with an MIC of 35.16µg/ml against P. aeruginosa and S. pyrogenes for KA 008 and 70.32 µg/ml against S. typhi and P. aeruginosa for KA 009. The acetylated derivatives showed the least activity against the test organisms. KA 008 also showed comparable activity against the standard Cefuroxime axetil used as the positive control.
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Dissertation submitted to The Department of Pharmaceutical Chemistry of The Faculty of Pharmacy and Pharmaceutical Sciences KNUST, in partial fulfilment of the requirements for the award of Master of Philosophy Degree in Pharmaceutical Chemistry.
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