A new diazo derivative of a pyrrolidine-2,5-dione (8) fused at position-3,4 to a dibenzobarrelene backbone has been prepared by coupling the previously reported N-arylsuccinimid (5) precursor with aryldiazonium ion of aniline. The initial step of the reaction involved the preparation of the intermediate 9,10-dihydro-9,10-ethanoanthracene-11,12-dicarboxylic anhydride (3) through [4 + 2]-cycloaddition between anthracene and maleic anhydride in refluxing xylene which was then condensed with para-aminophenol to give compound 5. Compounds 5 and 8 were characterized by their physical, elemental, and spectroscopic data. 2D-NMR (COSY, HSQC, and HMBC) techniques were used to confirm the structure of compound 5. Compounds 5 (MIC = 32–128 μg/mL) and 8 (MIC = 16–256 μg/mL) along with the precursor 3 (MIC = 64–128 μg/mL) displayed moderate to low antimicrobial activities against selected bacterial and fungal species when compared with those of nystatin (MIC = 0.50–2 μg/mL) and ciprofloxacin (MIC = 0.50–16 μg/mL) used as reference drugs.
Graphical Abstract
Background : The present study describes for the first time, the synthesis of two pyrrolidine-2,5-dione derivatives that belong to N-arylsuccinimid (compound 5) and of azo (compound 8) class of molecules. The initial step of the reaction involved the preparation of the intermediate compound (9R, 10R, 11S)-9, 10-dihydro-9, 10-[3, 4] furanoanthracene-12, 14-dione (3) through [4 + 2]-cycloaddition between anthracene and maleic anhydride in xylene which was then condensed with para-hydroxyaniline to give compound 5. Subsequent coupling of 5 with the aryldiazonium ion of aniline gave compound 8.Results: These compounds were characterized by their physical, elemental, and spectroscopic data. 2D-NMR (COSY, HSQC, and HMBC) techniques were used to complete the elucidation of their structures. Compounds 5 (MIC = 32–128µg/mL) and 8 (MIC = 16–256µg/mL) along with the precursor 3 (MIC = 64–128µg/mL) displayed moderate antimicrobial activities against selected bacterial and fungal species when compared with those of nystatin (MIC = 0.50–2µg/mL) and ciprofloxacin (MIC = 0.50–16µg/mL) used as reference drugs.Conclusion: The results of biological tests showed that compounds 3, 5, 8 possess antimicrobial activities. Although being less active than the compound taken as a reference, the azo compound has better antibacterial activity than the other two compounds especially on Staphylococcus aureus, V. choleraeSG24 and, V. choleraeCO6 strains. These results show that the azo function (N = N) is indeed a pharmacophore and would be responsible for the biological activity in the azo molecules.
The present work describes the synthesis, characterization, and evaluation of the antibacterial activity of a new poly azo compound resulting from the coupling of a previously reported N-arylsuccinimid precursor 5 with the diazonium ion of aniline. This azo compound was characterized using its physical, elemental, and 1D and 2D spectroscopic data. The novel azo compound 7 (minimum inhibitory concentration [MIC] = 16–32 μg/mL) showed higher antibacterial activity than its precursor 5 (MIC = 32–64 μg/mL), although it was low compared to the reference drug ciprofloxacin (MIC = 0.5–4 μg/mL).
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