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Synthesis and Antibacterial Activity of Caffeine Derivatives Containing Amino-Acid Fragments

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Chemistry of Natural Compounds Aims and scope

Cross-coupling of 8-bromocaffeine, 8-bromo-1-butyltheobromine, or 8-bromo-7-butyltheophylline with α-, β-, or ω-amino-acid methyl or t-butyl ester hydrochlorides in toluene in the presence of the catalytic system Pd(OAc)2·XantPhos and Cs2CO3 with microwave activation led to the formation of xanthine derivatives containing amino-acid fragments in the C-8 position. The antibacterial activity against Staphylococcus aureus and Bacillus cereus was studied.

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Acknowledgment

The work was financially supported by a Russian Science Foundation Grant (Project No. 18-13-00361). We thank the Khimiya Common Use Center, NIOCh, SB, RAS, for the spectral and analytical studies.

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Authors and Affiliations

  1. N. N. Vorozhtsov Novosibirsk Institute of Organic Chemistry, Siberian Branch, Russian Academy of Sciences, 9 Prosp. Akad. Lavrent’eva, Novosibirsk, 630090, Russia

    D. V. Reshetnikov, T. V. Rybalova, S. S. Patrushev & E. E. Shults

  2. Novosibirsk State Medical University, 2 Krasnyi Prosp, Novosibirsk, 630091, Russia

    L. G. Burova, E. A. Bondareva & A. N. Evstropov

  3. Novosibirsk State University, 1 Pirogova St, Novosibirsk, 630090, Russia

    S. S. Patrushev

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  1. D. V. Reshetnikov
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  2. L. G. Burova
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  4. E. A. Bondareva
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  7. E. E. Shults
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Correspondence to E. E. Shults.

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Translated from Khimiya Prirodnykh Soedinenii, No. 5, September–October, 2022, pp. 765–771.

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Reshetnikov, D.V., Burova, L.G., Rybalova, T.V. et al. Synthesis and Antibacterial Activity of Caffeine Derivatives Containing Amino-Acid Fragments. Chem Nat Compd 58, 908–915 (2022). https://doi.org/10.1007/s10600-022-03826-3

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  • DOI: https://doi.org/10.1007/s10600-022-03826-3

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