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International Journal of Medicinal Chemistry
Volume 2016, Article ID 9346585, 8 pages
Research Article

Syntheses and Antibiotic Evaluation of 2-[(2R,4R)-4-Carboxy-2-hydroxypyrrolidin-1-yl]carbonylbenzene-1,5-dicarboxylic Acids and 2-Carbamoylbenzene-1,5-dicarboxylic Acid Analogues

1Department of Chemistry, Ahmadu Bello University, Zaria 810001, Nigeria
2School of Chemistry and Physics, University of KwaZulu-Natal, Private Bag X 54001, Durban 4000, South Africa

Received 27 October 2015; Accepted 16 December 2015

Academic Editor: Gangadhar B. Bagihalli

Copyright © 2016 Abdulrazaq Tukur et al. This is an open access article distributed under the Creative Commons Attribution License, which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.


Our search for new antibiotics led to the syntheses and biological evaluation of new classes of dicarboxylic acid analogues. The syntheses involve nucleophilic addition of different substituted benzylamine, aniline, alkylamine, and 4-hydroxyl-L-proline with carbamoylbenzoic acid. The results of the antimicrobial activity as indicated by the zone of inhibition (ZOI) showed that Z10 is the most active against Pseudomonas aeruginosa (32 mm) and least active against Candida stellatoidea (27 mm) and Vancomycin Resistant Enterococci (VRE) (27 mm), while Z7 shows the least zone of inhibition (22 mm) against Methicillin Resistant Staphylococcus aureus (MRSA). The minimum inhibition concentration (MIC) determination reveals that Z10 inhibits the growth of tested microbes at a low concentration of 6.25 μg/mL, while Z9 and Z12 inhibits the growth of most microbes at a concentration of 12.5 μg/mL, recording the least MIC. The Minimum Bactericidal/Fungicidal Concentration (MBC/MFC) results revealed that Z10 has the highest bactericidal/fungicidal effect on the test microbes, at a concentration of 12.5 μg/mL, with the exception of Candida stellatoidea and Vancomycin Resistant Enterococci (VRE) with MBC/MFC of 25 μg/mL. The result of this investigation reveals the potential of the target compounds (Z13,5,712) in the search for new antimicrobial agents.