Synthesis and Antimicrobial Evaluation of N,N'-(4-Nitro-1,2-phenylene)diamide Derivatives

Beatrice N. Iwuala1*, James D. Habila1, Mohammed S. Sallau1
Department of Chemistry, Ahmadu Bello University Zaria, Nigeria.
Corresponding Author: [email protected] ; Tel: +2348153613465
Recieved Date: July 01, 2018; Accepted Date: July 23, 2018; Published Date: 10 August 2018
Citation: Iwuala BN, Habila JD, Sallau MS. Synthesis and Antimicrobial Evaluation of N,N-(4-Nitro-1,2-phenylene)diamide Derivatives.  Trop J Nat Prod Res. 2018; 2(8):383-387.
Copyright: © 2018 Iwuala et al. This is an open-access article distributed under the terms of the Creative Commons Attribution License, which permits unrestricted use, distribution, and reproduction in any medium, provided the original author and source are credited.

In the search for new antibiotics, 4-nitro-1,2-phenylenediamide analogues were synthesized via nucleophilic addition/elimination reaction of carboxylic acid derivatives with 4-nitro-1,2-phenylenediamine. In vitro antimicrobial assay of the analogues was done using the conventional broth dilution method on seven selected clinical isolates. The results of the zones of inhibition showed that N,N'-(4-nitro-1,2-phenylene)diacetamide (3a) has zones of inhibition ranging from 08 mm to 12 mm while (N,N'-(4-nitro-1,2-phenylene)dibenzamide (3c) has zones of inhibition ranging from 12 mm to 21 mm. N,N'-(4-nitro-1,2-phenylene)bis(2,2,2-trifluoroacetamide) (3d) was the most active against all tested organisms with zones of inhibition ranging from 11 mm in Pseudomonas aeruginosa to 34 mm in Methicillin-resistant Staphylococcus aureus (MRSA). The minimum inhibition concentration (MIC) determination reveals that 3d inhibits the growth of tested microbes at a concentration of 12.5 mg/mL with the exception of Klebsiella pneumonia in which the MIC was 25 mg/mL. The Minimum Bactericidal/Fungicidal Concentration (MBC/MFC) results revealed that 3d has the highest bactericidal effect on Pseudomonas aeruginosa, MRSA and Escherichia coli at a concentration of 12.5 mg/mL and was bacteriostatic/fungistatic against the rest of the organisms. The results observed clearly shows that molecules with electron withdrawing groups demonstrated better antibacterial activity.

Keywords: 4-nitro-1,2-phenylenediamine, carboxylic acid derivatives, antimicrobial activity and 4-nitro-1,2-phenylenediamide.
Back to Articles