Structural, Antimicrobial and in Silico Studies of Some Schiff Bases of Trans-paramethoxycinnamaldehyde Derivatives


  • G. U. Kaior University of Nigeria, Nsukka, Enugu State, Nigeria
  • N. J. Nwodo University of Nigeria, Nsukka, Enugu State, Nigeria
  • U. S. Oruma University of Nigeria, Nsukka, Enugu State, Nigeria
  • A. Ibezim University of Nigeria, Nsukka, Enugu State, Nigeria
  • A. E. Ochonogor University of Nigeria, Nsukka, Enugu State, Nigeria
  • K. K. Onyia University of Nigeria, Nsukka, Enugu State, Nigeria
  • Nnamdi L. Obasi University of Nigeria, Nsukka, Enugu State, Nigeria


Trans-paramethoxycinnamaldehyde;2,4-diaminobenzoic acid;2-aminophenol; 1,8-diamino-3,6-dioxaoctane, binding poses


Communication in Physical Sciences 2020, 5(4): 544-566

Received 29 May 2020/Accepted 29 July 2020

Three Schiff bases viz; 3,5-bis[(E)-[(2E)-3-(4-methoxyphenyl)prop-2-en-1-ylidene]benzoic acid (3,5-DA), 2-[(E)-[(2E)-3-(4-methoxyphenyl)prop-2-en-1-ylidene]amino]phenol (OAP) and [3-(4-methoxy-phenyl)-allylidene]-[2-(2-{2-[3-(4-methoxy-phenyl)-allylideneamino]-ethoxy}-ethoxy)-ethyl]-amine (TPMC/DDE) are reported. The Schiff bases were synthesized from the condensation reaction of trans-paramethoxycinnamaldehyde and the primary amines (3,5-diaminobenzoic acid, 2-aminophenol and 1,8-diamino-3,6-dioxaoctane respectively), in dry methanol. The synthesized Schiff bases were characterized using UV-Visible, Fourier transform infrared (FTIR), 1H, and 13C NMR spectroscopies. The In vitro antimicrobial screening of the Schiff bases were carried out on gram-positive bacteria: (Staphylococcus aureus and Bacillus subtillus) and gram-negative bacteria: (Pseudomonasaeruginosa, and Escherichia. coli strain13) and against the fungi, Aspergillus niger and Candida albicans using the agar well diffusion method. The ligands 3,5-DA and OAP only showed activity against the fungus, Candida albicans with inhibition zone diameter (IZD) of 10 mm and minimum inhibitory concentrations (MIC) of 5.0 mg/mL and 3.0 mg/mL respectively. The ligand, TPMC/DDE also showed varying activity against the bacteria, Pseudomonas aeroginosa with an IZD of 8.0 mm and MIC of 7.5 mg/mL while Escherichia coli displayed inhibition with an IZD of 10.0 mm and MIC of 1.9 mg/mL. According to molecular docking studies, the binding affinity of the compounds towards two validated antibiotic and antifungal drug targets (DD-transpeptidase–DDPT and N-myristyol transferase-NMT) were in agreement to their observed in vitro antimicrobial activities. Moreover, their retrieved binding poses explained intermolecular forces behind the interactions that exist between the proteins and the ligands, a knowledge which is very useful in structural modification for activity optimization.



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Author Biographies

G. U. Kaior, University of Nigeria, Nsukka, Enugu State, Nigeria

Department of Pure and Industrial Chemistry

N. J. Nwodo, University of Nigeria, Nsukka, Enugu State, Nigeria

Department of Pharmaceutical and Medicinal Chemistry

U. S. Oruma, University of Nigeria, Nsukka, Enugu State, Nigeria

Department of Pure and Industrial Chemistry

A. Ibezim, University of Nigeria, Nsukka, Enugu State, Nigeria

Department of Pure and Industrial Chemistry

A. E. Ochonogor, University of Nigeria, Nsukka, Enugu State, Nigeria

Department of Pure and Industrial Chemistry

K. K. Onyia, University of Nigeria, Nsukka, Enugu State, Nigeria

Department of Pure and Industrial Chemistry

Nnamdi L. Obasi, University of Nigeria, Nsukka, Enugu State, Nigeria

Department of Pure and Industrial Chemistry


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