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New Thiazole-Bearing Oxadiazole Derivatives: Synthesis, Thymidine Phosphorylase Inhibitory Potential, and Molecular Docking Study

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Abstract

A series of sixteen oxadiazole derivatives containing a thiazole ring were synthesized, characterized by different spectroscopic techniques (1H and 13C NMR, EI HRMS) and evaluated for their in vitro thymidine phosphorylase inhibitory activity. All compounds showed good to excellent thymidine phosphorylase inhibitory activity with IC50 values ranging between 32.40±0.01 to 54.10±0.02 µM, and three of them proved to be more active than the standard drug 7-deazaxanthine (IC50 = 38.68±1.12 µM). Molecular docking study was carried out on the most active compounds in order to identify their interactions with the active site of the enzyme. Structure–activity relationship was also analyzed on the basis of substitution pattern on the phenyl ring.

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Funding

The authors thank the Higher Education Commission of Pakistan for providing a research grant under National Research Program for Universities (project nos. 5721, 5092).

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Authors and Affiliations

  1. Department of Chemistry, University of Okara, 56300, Okara, Punjab, Pakistan

    H. Ullah & S. Ullah

  2. Department of Chemistry, Hazara University, 21300, Mansehra, Khyber Pakhtunkhwa, Pakistan

    F. Khan & F. Rahim

  3. Department of Clinical Pharmacy, Institute for Research and Medical Consultations (IRMC), Imam Abdulrahman Bin Faisal University, 31441, Dammam, Saudi Arabia

    M. Taha

  4. Department of Zoology, Faculty of Life Science, The Women University Multan, 66000, Multan, Punjab, Pakistan

    M. Sarfraz

  5. Institute of Biological Sciences, Sarhad University of Science and Information Technology, 25000, Peshawar, Pakistan

    A. Aziz

  6. Center of Nanoscience, University of Okara, 56300, Okara, Punjab, Pakistan

    M. U. Khan

  7. Department of Biochemistry, University of Okara, 56300, Okara, Punjab, Pakistan

    M. Ullah

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  1. H. Ullah
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Ullah, H., Khan, F., Taha, M. et al. New Thiazole-Bearing Oxadiazole Derivatives: Synthesis, Thymidine Phosphorylase Inhibitory Potential, and Molecular Docking Study. Russ J Org Chem 57, 1993–2001 (2021). https://doi.org/10.1134/S1070428021120150

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  • DOI: https://doi.org/10.1134/S1070428021120150

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