Novel vanillin derivatives: Synthesis, anti-oxidant, DNA and cellular protection properties
Abstract Antioxidants have been the subject of intense research interest mainly due to their beneficial properties associated with human health and wellbeing. Phenolic molecules, such as naturally occurring Resveratrol and Vanillin, are well known for their anti-oxidant properties, providing a starting point for the development of new antioxidants. Here we report, for the first time, the synthesis of a number of new vanillin through the reductive amination reaction between vanillin and a selection of amines. All the compounds synthesised, exhibited strong antioxidant properties in DPPH, FRAP and ORAC assays, with compounds 1b and 2c being the most active. The latter also demonstrated the ability to protect plasmid DNA from oxidative damage in the presence of the radical initiator AAPH. At cellular level, neuroblastoma SH-SY5Y cells were protected from oxidative damage (H 2 O 2 , 400 μM) with both 1b and 2c. The presence of a tertiary amino group, along with the number of vanillin moieties in the molecule contribute for the antioxidant activity. Furthermore, the delocalization of the electron pair of the nitrogen and the presence of an electron donating substituent to enhance the antioxidant properties of this new class of compounds. In our opinion, vanillin derivatives 1b and 2c described in this work can provide a viable platform for the development of antioxidant based therapeutics. Highlights Facile synthesis of new Vanillin derivatives based on reductive amination reaction. High Anti-oxidant/radical scavenging properties of most compounds when compared to parent compound vanillin. DNA protective properties of synthesised derivatives against free radical inducer. Cyto-protective activity of selected Vanillin derivatives against Oxidative damage. Potential platform for the development of antioxidant based therapeutics. Graphical abstract [DISPLAY OMISSION]
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