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Synthesis, characterization and antimicrobial properties of two derivatives of pyrrolidine-2,5-dione fused at positions-3,4 to a dibenzobarrelene backbone

Synthesis, characterization and antimicrobial properties of two derivatives of pyrrolidine-2,5-dione fused at positions-3,4 to a dibenzobarrelene backbone

Authors :
Emmanuel Sopbué Fondjo
Abdou Salamou Njoya
Jean-de-Dieu Tamokou
Giscard Doungmo
Bruno Ndjakou Lenta
Peter F. W. Simon
Apollinaire Tsopmo
Jules-Roger Kuiate
Source :
BMC Chemistry, Vol 16, Iss 1, Pp 1-10 (2022)
Publication Year :
2022
Publisher :
BMC, 2022.

Abstract

Abstract 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

Details

Language :
English
ISSN :
2661801X
Volume :
16
Issue :
1
Database :
Directory of Open Access Journals
Journal :
BMC Chemistry
Publication Type :
Academic Journal
Accession number :
edsdoj.feb0f61739e840bdbecaf3647401bc47
Document Type :
article
Full Text :
https://doi.org/10.1186/s13065-022-00801-5