Chalcones are known to represent the core structure of natural and synthetic compounds with high pharmaceutical and/or biomedical activities. Curcumin is a natural chalcone found in the plant Curcuma longa, widely cultivated in India. This compound is recognized as being antioxidant, antibacterial, anti-inflammatory, anti-cancer, among many others. Curcumin have been reported to possess an antioxidant activity more potent than vitamin E and also to induce apoptosis in tumor cells. Studies have even suggested the use of curcumin to treat neurodegenerative diseases as Parkinson's and Alzheimer’s. Unfortunately, the curcumin bioavailability is low because of its poor absorption, limited tissue distribution, rapid metabolism, short half-life, water insolubility and instability in gastrointestinal tract. As an alternative, we proposed the synthesis of curcumin analogues incorporating ferrocene moiety. This organometallic compound has already showed to enhance pharmacological properties of different compounds and previously established drugs. We believed that incorporation of the ferrocene moiety will improve the analogues bioavailability and biomedical applications. The purpose of these project is to study the bioactivity of vanillin and isovanillin derivatives and compare them in order to determine how the aromatic substitution affect the compounds activity. A total of four ferrocenyl curcumin analogues have been synthesized by Claisen-Schmidt condensation. Preliminary results on the vanillin-derived compound exhibited antibacterial potential against gram-positive bacteria S. staphylococcus, S. aureus, B. cereus and the gram-negative K. pneumoniae with a minimum inhibitory concentration less than 1.95um. Also showed that another one of the compounds is more efficient as a radical scavenger than ascorbic acid.

Synthesis and characterization of ferrocenyl curcumin analogues as potential antioxidant and antibacterial compounds

253rd National Meeting (2017)

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