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Two benzoxazine derivatives (3a and 3b) interact with biological targets to study their antioxidant and anticancer effects. Substitution with a hydrogen atom enabled compound 3a to inhibit DPPH radicals more effectively than ascorbic acid, with a lower EC50 value. In silico investigations showed that the compounds boundspontaneously to glutathione peroxidase 7 via conventional hydrogen hydrogen bonds, suggesting that they could neutralize reactive oxygen species. Compound 3a could induce single-stranded DNA conformation in vitro. Binding energies similar to the in vitro results suggested specific, minor interaction mechanisms in docking experiments. Increased absorbance at 280 nm and electrostatic binding of the compounds to BSA suggest their anticancer potential.anticancer potential. These results shed light on the pharmacological processes and medicinal potential of benzoxazine derivatives.Key words: Benzoxazine derivatives, antioxidant activity, antitumor potential, DNA, BSA, Molecular docking.

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