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Design, combinatorial synthesis and cytotoxic activity of 2-substituted furo[2,3-d]pyrimidinone and pyrrolo[2,3-d]pyrimidinone library

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Abstract

A facile protocol was developed for the combinatorial synthesis of furo[2,3-d]pyrimidinone and pyrrolo[2,3-d]pyrimidinone library via a one-pot condensation, from 2-amino furans/pyrroles. Herein reported process required a similar reaction condition, providing mild access to two diverse series of natural product-like heterocycles. Both furo[2,3-d]pyrimidinones and pyrrolo[2,3-d]pyrimidinones were evaluated in vitro against a panel of human cancer cell lines including against human cancer HeLa (cervical), MCF-7 (breast) and HT-29 (colon) cell lines. Derivative 12n ((2-(4-chlorophenyl)-1-methyl-6,7,8,9-tetrahydropyrido[1,2-a]pyrrolo[2,3-d]pyrimidin-4(1H)-one)) showed high activity (IC50 = 6.55 ± 0.31 µM) against the HeLa cell line. These products could be subjected to a various modification and therefore represent important skeletons for the anticancer drug discovery.

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Acknowledgements

This work was financially supported by the National Key R&D Program of China (No. 2020YFE0205600), and by “CAM Resources Data Base” in National Basic Science Data Center (No. NBSDC-DB-19).

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Authors and Affiliations

  1. State Key Laboratory Basis of Xinjiang Indigenous Medicinal Plants Resource Utilization, Xinjiang Technical Institute of Physics and Chemistry, Chinese Academy of Sciences, South Beijing Rd 40-1, Urumqi, 830011, People’s Republic of China

    Buer Song, Lifei Nie, Khurshed Bozorov, Jiangyu Zhao & Haji Akber Aisa

  2. University of Chinese Academy of Sciences, 19 A Yuquan Rd, Beijing, 100049, People’s Republic of China

    Buer Song & Haji Akber Aisa

  3. Faculty of Chemistry, Samarkand State University, University blv. 15, Samarkand, Uzbekistan, 140104

    Khurshed Bozorov & Rustamkhon Kuryazov

  4. Urgench State University, Kh. Olimjon st. 14, Urgench, Uzbekistan, 220100

    Rustamkhon Kuryazov

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Song, B., Nie, L., Bozorov, K. et al. Design, combinatorial synthesis and cytotoxic activity of 2-substituted furo[2,3-d]pyrimidinone and pyrrolo[2,3-d]pyrimidinone library. Mol Divers 27, 1767–1783 (2023). https://doi.org/10.1007/s11030-022-10529-y

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