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Syntheses, characterization, antimicrobial and in-silico studies of schiff-bases of transparamethoxycinnamaldehyde derivatives


Joint Event on 4th Pharmaceutical Chemistry Conference & 12th World congress on Future Pharma

June 27-28, 2019 | Amsterdam, Netherlands

Akachukwu Ibezim, Kaior G U, Obasi N L, Oruma U S, Michael Lutter, Klaus Jurkschat, Nwodo N J and Ponnadurai Ramasami

University of Nigeria, Nsukka, Nigeria Technical University, Dortmund, Germany University of Mauritius, Mauritius University of Johannesburg Doornfontein Campus, South Africa

Posters & Accepted Abstracts: Pharmaceutical Analysis

Abstract

A series of new Schiff bases was prepared. The compounds were synthesized from the condensation reaction of trans-p-methoxycinnamaldehyde and the primary amines 2, 4-diaminobenzoic acid, 2-aminophenol and 1, 8-diamino-3, 6-dioxaoctane, respectively, in dry methanol and characterized by UV, FTIR, 1H and 13C NMR spectroscopy. Electronic spectra showed two absorption bands which were assigned to n-δ* and n-𝜋* transitions. Five vibrational modes were observed in the FT-IR spectra within range of 1598-1637 cm-1 v(C=N), 1613-1783 cm-1 v(C=C), 3504-3690 cm-1 v(O-H), 3117-3182 cm-1 v(C-H) aromatic and a sharp peak at 1942 cm-1 which was assigned to C=O of CO2H. 1H NMR spectra identified H-C=N, H-C=C(H)-C, CO2H, CH3-O, -OH and phenyl protons within range of δH 6.69-9.62 ppm, 5.99-6.98 ppm, 6.33 ppm, 2.09- 3.86 ppm, 8.39 ppm, 6.81-7.94 ppm, respectively. 13C NMR showed the presence of C=N, O-CH3, CO2H, CH2-CH2, phenyl carbon resonance within range of δC 159.25-167.68 ppm, 55.87-5597 ppm, 174.24 ppm, 60.89-71.62 ppm and 115.49-162.50 ppm, respectively. Docking calculations and biological screening against Pseudomonas aeruginosa, Escherichia coli, Staphylococcus aureus, Bacillus subtilis, Aspergillus niger, Candida albican were used to test for the antimicrobial activity. The computed dock-scores of the compounds toward bacterial transpeptidase and fungal N-myristoyl transferase were within range of -8.33 to -8.92 Kcal/mol and -11.24 to -12.99 Kcal/mol, respectively; all the compounds were active against C. albican at 1.6-5.0 mg/ml MIC range while only TPMC/DDE had activity against P. aeruginosa and E. coli out the studied bacteria at MIC range of 1.9-7.5 mg/ml which provides the bases to further consider TPMC/DDE in effort to develop new antimicrobial agent.

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