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Synthesis, Molecular Modeling, and Antioxidant Activity of New Thiadiazole-Triazole Analogs Hybridized with Thiophene

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Abstract

The synthetic protocol of our targeted thiadiazole-triazole analogs hybridized with thiophene is based on heterocyclization key compound 5-(2-chloroacetamido)-2-phenyl-N-(1,3,4-thiadiazol-2-yl)-2H-1,2,3-triazole-4-carboxamide (1) in the presence of different thiocarbamoyl reagents 2, 5, and/or 8. The HOMO–LUMO energies and Fukui’s indices were established by applying the DFT/B3LYP molecular modeling methodology. The examined compounds exhibited a low and close HOMO–LUMO energy gap of 1.64–1.99 eV, where the derivatives 7 and 4 presented the lowest and highest values, respectively. The antioxidant properties of the prepared thiadiazole–triazole–thiophene hybrids were investigated using the DPPH radical scavenging technique, where hybrids 4 and 6 showed the strongest inhibition, whereas analog 10 showed only moderate inhibition. Over the course of two common reference drugs, vitamin C and BHT, all of the radical scavenging for thiadiazole-triazole hybrids was examined. Additionally, the generated thiadiazole–triazole–thiophene hybrids' molecular docking was evaluated through the PDB code 3MNG. Hybrid 6 had the highest recorded binding score when compared to the other hybrids. The docking repercussions were appropriate and addressed with the antioxidant assessment.

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Acknowledgements

The authors would like to thank the Deanship of Scientific Research at Umm Al-Qura University for supporting this work by Grant Code: (22UQU4350527DSR12).

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Authors and Affiliations

  1. Department of Chemistry, Faculty of Applied Science, Umm Al Qura University, Makkah, 24230, Saudi Arabia

    Abrar Bayazeed, Amerah Alsoliemy, Jihan Qurban & Nashwa M. El-Metwaly

  2. Department of Chemistry, College of Science, Taibah University, Al-Madinah Al-Munawarah, 30002, Saudi Arabia

    Khalid Althumayri

  3. Department of Chemistry, Faculty of Science, King Khalid University, Abha, 62529, Saudi Arabia

    Sraa Abu-Melha

  4. Department of Chemistry, College of Science, Taibah University, P.O. Box 344, Madinah, Saudi Arabia

    Rua B. Alnoman

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  1. Abrar Bayazeed
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Correspondence to Nashwa M. El-Metwaly.

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Bayazeed, A., Althumayri, K., Abu-Melha, S. et al. Synthesis, Molecular Modeling, and Antioxidant Activity of New Thiadiazole-Triazole Analogs Hybridized with Thiophene. Arab J Sci Eng 48, 7553–7570 (2023). https://doi.org/10.1007/s13369-022-07572-0

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