Volume 8 ; Issue 2 ; in Month : July-Dec (2024) Article No : 182
Oladimeji OH, Uduak SJ, Sunday NC.

Abstract

Background: Schiff bases are a class of organic compounds referred to as imines and characterised by a carbon-nitrogen double bond. Their versatility and exhibition of a broad spectrum of biological activities such as antioxidant, antibacterial, antifungal, antiviral, anti-malarial, anti-inflammatory and anticancer amongst many others contribute to their significance in organic chemistry. Objectives: The harmful effects of free radicals to the human body and the ever worrisome prevalence of microbial resistance to anti-infective drugs currently in clinical therapy led to the search for new molecules with possibly better activities for treating/ameliorating disease conditions. This search for novel pharmaceutically active compounds with the aim of mitigating these conditions threw up the choice of Schiff base synthesis using vanillin and two alkyl amines. Methodology: Vanillin was reacted separately with these amines leading to Schiff bases in the presence of acid. The melting points, refractive indices and optical rotations of the vanillin and the resultant bases were obtained. The antioxidant activity (IC50) of these compounds was evaluated using the DPPH (2, 2-diphenyl-1-picrylhydrazyl hydrate) assay test. A comparison of the antioxidant activities so obtained was done to determine if the synthesized bases would show better activities than vanillin and Vitamin C. The agar diffusion method was adopted for screening the compounds against Staphylococcus aureus, Escherichia coli and Candida albicans for both antibacterial and antifungal potentials respectively. Results: A combination of physico-chemical determinations and IR spectral technique have revealed that both synthesized imines are new. Consequently, their nomenclatures are vanillyl hexyl imine (1-iminohexyl-3-methoxy-4-hydroxy benzene) (Iyadimine A) and vanillyl heptyl imine (1-iminoheptyl-3-methoxy-4-hydroxy benzene) (Iyadimine B ) respectively. Vanillin demonstrated a moderate antioxidant activity of IC50 of 0.52 µg/mL which compare favourably with 0.48 µg/mL shown by Vitamin C. However, both Iyadimine A and Iyadimine B were marginally active at 1.93 and 1.03 µg/mL respectively. Interestingly, Iyadimine B was slightly more antioxidant on account of the longer heptyl chain which makes it more lipophillic than Iyadimine A with the hexyl moiety rendering it less lipophillic. Both the antibacterial and antifungal activities elicited by the imines showed concentration-dependency. Furthermore, Iyadimine A was more antibacterial against S. aureus than E. coli while the converse was observed with Iyadimine B. However both were remarkably suppressive of C. albicans. Conclusion: The results from this study indicate that two newly synthesized vanillyl imines demonstrated marginal antioxidant activities. Furthermore both bases also showed good antibacterial and antifungal activities. Hence, the two compounds could be promising lead drug templates in the search for newer and more efficacious biological agents especially in synergistic antimicrobial co-administration and formulation studies in drug development.

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