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Synthesis, Crystal Structure, and DFT Study of a New Derivative of Pyrido[2,3-d]pyrimidine

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Abstract

N-{4-[(6-bromopyrido[2,3-d]pyrimidin-4-yl)oxy]phenyl}morpholine-4-carboxamide has been synthesized as a derivative of pyrido[2,3-d]pyrimidine that demonstrates antitumor, antibacterial, anti-inflammatory, and antimicrobial activities. Synthesis of the target compound based on 2-aminonicotinic acid as the starting material has included its esterification, bromination, cyclization, and substitution reactions. Structure of the product is confirmed by 1H and 13C NMR, FT-IR, and single-crystal X-ray diffraction (XRD). The optimized structure, electrostatic potential and frontier molecular orbitals (FMO) of the compound have been approached by DFT calculations. The compound demonstrates antiproliferative activity on A375 cells.

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ACKNOWLEDGMENTS

This work has been awarded the Guizhou Provincial Natural Science Foundation ([2020]1Y393).

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Authors and Affiliations

  1. School of Chemistry and Chemical Engineering, Guizhou University, 550025, Guiyang, China

    Liyuan Deng, Wanpeng Liao & Hongyan Pan

  2. Guizhou Engineering Laboratory for Synthetic Drugs, 550025, Guiyang, China

    Liyuan Deng, Hong Sun, Weiyin Hu, Wanpeng Liao & Zhixu Zhou

  3. School of Pharmaceutical Sciences, Guizhou University, 550025, Guiyang, China

    Hong Sun, Weiyin Hu & Zhixu Zhou

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  1. Liyuan Deng
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  2. Hong Sun
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  3. Weiyin Hu
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  4. Wanpeng Liao
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  5. Zhixu Zhou
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  6. Hongyan Pan
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Correspondence to Zhixu Zhou or Hongyan Pan.

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Deng, L., Sun, H., Hu, W. et al. Synthesis, Crystal Structure, and DFT Study of a New Derivative of Pyrido[2,3-d]pyrimidine. Russ J Gen Chem 91, 2489–2496 (2021). https://doi.org/10.1134/S1070363221120197

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