Synthesis, Characterization of Pyrano-[2,3-c]-Pyrazoles Derivatives and Determination of Their Antioxidant Activities
Authors:   Department of Biology, Laboratory of Physiopathology, Genetics, Molecular and Biotechnology (PGMB), Faculty of Sciences Aïn Chock, Research Center of Health and Biotechnology, Hassan II University of Casablanca, Casablanca, Morocco., Addoum Boutaina , El khalfi Bouchra ,   Department of Biology, Laboratory of Physiopathology, Genetics, Molecular and Biotechnology (PGMB), Faculty of Sciences Aïn Chock, Research Center of Health and Biotechnology, Hassan II University of Casablanca, Casablanca, Morocco., Idiken Mohamed ,   Department of Biology, Laboratory of Physiopathology, Genetics, Molecular and Biotechnology (PGMB), Faculty of Sciences Aïn Chock, Research Center of Health and Biotechnology, Hassan II University of Casablanca, Casablanca, Morocco., Sakoui Souraya ,   Department of Biology, Laboratory of Physiopathology, Genetics, Molecular and Biotechnology (PGMB), Faculty of Sciences Aïn Chock, Research Center of Health and Biotechnology, Hassan II University of Casablanca, Casablanca, Morocco., Derdak Reda ,   Department of Biology, Laboratory of Physiopathology, Genetics, Molecular and Biotechnology (PGMB), Faculty of Sciences Aïn Chock, Research Center of Health and Biotechnology, Hassan II University of Casablanca, Casablanca, Morocco., Aniq Filali Ouafaa ,   Department of Biology, Laboratory of Physiopathology, Genetics, Molecular and Biotechnology (PGMB), Faculty of Sciences Aïn Chock, Research Center of Health and Biotechnology, Hassan II University of Casablanca, Casablanca, Morocco., Elmakssoudi Abdelhakim ,   Department of Chemistry, Laboratory of Organic Synthesis, Extraction, and Valorization, Faculty of Sciences Aïn Chock, Hassan II University of Casablanca, Casablanca, Morocco., Soukri Abdelaziz ,   Department of Biology, Laboratory of Physiopathology, Genetics, Molecular and Biotechnology (PGMB), Faculty of Sciences Aïn Chock, Research Center of Health and Biotechnology, Hassan II University of Casablanca, Casablanca, Morocco.
Published: July 2021

Background: Antioxidants are developed to assist the immune system and overcome oxidative stress, the aggression of cellular constituents due to imbalance between reactive oxygen species and the inner antioxidant system. The main objective of this study was to search for new and potent antioxidants to protect humans against diseases associated with oxidative stress. Methods: In this study, three pyrano-[2,3-c]-pyrazole derivatives were synthesized via Multicomponent Reaction (MCR) approach and were characterized, using a melting point, High-Performance Liquid Chromatography (HPLC), and spectroscopic analyses (IR; 1H-NMR; 13C-NMR). All of the generated compounds were screened for their antioxidant properties in vivo, using ciliate “Tetrahymena” as a model organism exposed to oxidative and nitrative stress. They were then studied in vitro by using 1,1-diphenyl-2-picrylhydrazyl (DPPH) assays. Results: The results demonstrated that the three compounds (5a, b, c) are biologically active and possess potent antioxidant activities, especially the 5a and 5b derivatives. On the other hand, the in vitro bioassays revealed that the 5a derivative possessed a significant antioxidant activity much greater than ascorbic acid. Accordingly, the in silico data are consistent with the experimental data. Conclusion: These findings confirmed the potent antioxidant property of the synthesized compounds, providing us with new inspiration and challenges to design a library of pharmaceutical compounds with strong activity and low toxicity in the future.