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Green synthesis and 3D pharmacophore study of pyrimidine and glucoside derivatives with in vitro potential anticancer and antioxidant activities

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Abstract

A facile and an efficient one-pot green synthesis of pyrimidine derivatives using the environmentally friendly Cerium(IV) ammonium nitrate (CAN) as catalyst and water as a solvent has been described. Some of the synthesized pyrimidines react with 2,3,4,6-tetra-O-acetyl-α-d-glucopyranosyl bromide in ethanol containing potassium hydroxide to give S-glucoside derivatives. The structures of the newly synthesized compounds were elucidated on the basis of their spectral and elemental analyses. In addition, selected derivatives of the products were screened for their anticancer activities against four tumor cell lines using MTT assay and the results showed that some of these compounds have potent cytotoxic effect, as concluded from their IC50 values. Molecular modeling studies including generation of a 3D pharmacophore model were carried out. The study showed high correlation with the experimental results. Antioxidant activity of the synthesized products was also investigated and most of them showed potent activity.

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Acknowledgements

We gratefully acknowledge the financial support of Ain-Shams University, Benha University and Science & Technology Development Fund (STDF), Ministry of Scientific Research (Egypt) through project 25410.

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Authors and Affiliations

  1. Synthetic Heterocycles laboratory, Chemistry Department, Faculty of Science, Ain Shams University, P. O. Box 11566, Cairo, Egypt

    Mounir A. Salem

  2. Chemistry Department, Faculty of Science, Benha University, P. O. Box 13518, Benha, Egypt

    Mohamed S. Behalo

  3. Pharmaceutical Chemistry Department, Faculty of Pharmacy, Ain Shams University, P. O. Box 11566, Cairo, Egypt

    Eman Elrazaz

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  1. Mounir A. Salem
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  2. Mohamed S. Behalo
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Correspondence to Mohamed S. Behalo.

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Salem, M.A., Behalo, M.S. & Elrazaz, E. Green synthesis and 3D pharmacophore study of pyrimidine and glucoside derivatives with in vitro potential anticancer and antioxidant activities. Med Chem Res 28, 1223–1234 (2019). https://doi.org/10.1007/s00044-019-02367-9

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