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Facile Regioselective Synthesis, Molecular Dynamics Study, and Antioxidant Activity of Some 3′H,4H-Spiro[chromene-3,2′-[1,3,4]thiadiazol]-4-ones

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Abstract

A series 3′H,4H-spiro[chromene-3,2′-[1,3,4]thiadiazol]-4-ones 6a–6d were synthesized regioselec­tively through the thermolysis of spiro[benzopyran-3′,2-[1,3,4]oxadithiino[5,6-c]benzopyran]-4′-ones 5a–5d in the presence of ethyl diazoacetate. The new products were characterized by different spectroscopic techniques, and their antioxidant activity was evaluated by the DPPH free radical scavenging assay using ascorbic acid as a reference drug. One of the synthesized compounds showed the highest inhibition percentage (80.8±0.8%). The results of molecular docking studies were consistent with the in vitro antioxidant activity.

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ACKNOWLEDGMENTS

The spectral data were obtained using the facilities of the Central Services Laboratory, National Research Center, (Dokki, Cairo, Egypt). Elemental analysis was performed at the Microanalysis Center, Cairo University (Cairo, Egypt).

Funding

This study was funded by the National Research Centre, Dokki, Giza, Egypt (project no. 13010101).

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Authors and Affiliations

  1. Photochemistry Department, National Research Centre, 12622, Dokki, Giza, Egypt

    T. El Malah & M. I. Hegab

  2. Chemistry of Natural and Microbial Products Department, National Research Centre, 12622, Dokki, Giza, Egypt

    I. S. Abd-Elsalam, A. M. Saleh & A. A. El-Rashedy

Authors
  1. T. El Malah
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  2. I. S. Abd-Elsalam
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  3. A. M. Saleh
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  4. A. A. El-Rashedy
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  5. M. I. Hegab
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Correspondence to M. I. Hegab.

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Malah, T.E., Abd-Elsalam, I.S., Saleh, A.M. et al. Facile Regioselective Synthesis, Molecular Dynamics Study, and Antioxidant Activity of Some 3′H,4H-Spiro[chromene-3,2′-[1,3,4]thiadiazol]-4-ones. Russ J Org Chem 59, 1206–1213 (2023). https://doi.org/10.1134/S1070428023070126

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