Comparative Study of Synthesis, Structural and Antioxidant Activity In Vitro of Some New Carboxylic α,α-diaminodiesters Derivatives



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Submitted Jun 19, 2021
Published Jul 13, 2021
10.24018/ejchem.2021.2.3.64

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Considering the richness of heterocyclic chemistry, and the diversity of applications it possesses, in the present work we were interested in preparing new polyfunctional α,α-diaminodiesters derived from glycine, via the N-alkylation reaction of methyl 2-azido-2-benzamidoacetate with a series of heterocyclic and non-heterocyclic carboxylic aminoesters, using different bases. The structures of the synthesized molecules were characterized by 1D and 2D NMR spectroscopy, mass spectrometry (MS-ESI) and elemental analysis. Two compounds from this series were isolated as single crystals and their chemical structures were determined by X-ray diffraction. The antioxidant effect of the synthesized compounds was tested in vitro using the free radical scavenging power (DPPH) and reducing power (FRAP) tests. The results show that the different extracts tested have a relatively high antioxidant power compared to the positive control considered, especially for the compound methyl 2-benzamido-2-(2-methoxy-2-oxo-1-phenylethyl)amino)acetate, which showed a very strong antiradical power and reducing power.

Keywords: N-alkylation, α,α-diaminodiesters, antioxidant activity, DPPH, FRAP

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