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Paper Details

Antioxidant and Metal Chelation Efficiency of Chalcone Derivatives

*M. Rajendran and M. Thiruppathi Devi

Journal Title:Journal of Chemical, Biological and physical sciences

Several chalcone derivatives have found pharmaceutical uses. During heavy metal stress phenolic compounds can act as metal chelators and on the other hand phenolics can directly scavenge molecular species of active oxygen. The antioxidant activity of chalcone was believed to increase due to electron donating substituent in the ring para position. Two chalcones have been synthesised by condensing 2-hydroxyacetophenone with different aromatic aldehydes. The synthesized chalcones such as 2-hydroxy-4-methoxychalcone (4MeC) and (2-hydroxy-4-chlorochalcone (4ClC) can be used as antioxidant and chelating agent. The formation constants of chalcones of transition metal ions have been studied by using Jobs method. The chelating potential of the complexation of chalcones with Fe(II), Co(II), Ni(II) and Zn(II) was investigated by UV-Vis spectroscopy. The comparison of binding efficiency of the two chalcones 4MeC and 4ClC with various divalent metal ions reveals the fact that 4MeC has an increasing binding towards metals than the 4ClC. The antioxidant activity of these chalcones has been tested by adopting DPPH assay. It has been found that the 4MeC have higher antioxidant activity and metal chelation property than 4ClC. We have studied the properties of two chalcones, 4MeC and 4ClC, using semiempirical method using Parametric Model 3 (PM3) method and to understand the fundamental differences between the two molecules. The computed ionization potential and electron affinity showed that chalcones have a low molecular hardness and thus have a property to dissociate its phenolic OH and the resulting charge undergoes delocalization throughout the structure. When the substituent group attached at the fourth position ofchalcone was changed from electron donating group (EDG) to electron withdrawing group (EWG), the O-H BDE increased.