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Efficient method for the synthesis of novel substituted thieno[2,3-d]pyrimidine-4-carboxylic acids, their derivatization, and antimicrobial activity

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Chemistry of Heterocyclic Compounds Aims and scope

An effective method for accessing novel substituted thieno[2,3-d]pyrimidine-4-carboxylic acids in 63–71% yields based on Pd(dppf)Cl2-catalyzed carbonylation of substituted 4-chlorothieno[2,3-d]pyrimidines has been proposed; a procedure has been developed for obtaining the amides of these acids, suitable for liquid-phase combinatorial synthesis, in 53–77% yields. Compounds with antimicrobial activity against Pseudomonas aeruginosa similar to the reference drug streptomycin were found among the synthesized amides.

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The authors are grateful to Enamine Ltd. for providing the equipment for carrying out reactions in autoclaves and registration of 1H, 13C NMR and LC-MS spectra of the synthesized compounds.

The authors also thank the head of the laboratory of biochemistry and biotechnology of Mechnikov Institute of Microbiology and Immunology of the National Academy of Medical Sciences of Ukraine (Kharkiv) Candidate of Biological Sciences Senior Researcher T. P. Osolodchenko for conducting the antimicrobial activity test of the synthesized compounds.

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Authors and Affiliations

  1. National University of Pharmacy, 53 Pushkinska St, Kharkiv, 61002, Ukraine

    Olena D. Vlasova, Volodymyr I. Kabachnyy & Sergiy V. Vlasov

  2. Enamine Ltd., 78 Krasnotkatska St, Kyiv, 02094, Ukraine

    Konstantin Yu. Krolenko, Maxim A. Nechayev & Pavlo E. Shynkarenko

Authors
  1. Olena D. Vlasova
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  2. Konstantin Yu. Krolenko
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  3. Maxim A. Nechayev
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  4. Pavlo E. Shynkarenko
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  5. Volodymyr I. Kabachnyy
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  6. Sergiy V. Vlasov
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Correspondence to Olena D. Vlasova.

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Translated from Khimiya Geterotsiklicheskikh Soedinenii, 2019, 55(2), 184–188

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Vlasova, O.D., Krolenko, K.Y., Nechayev, M.A. et al. Efficient method for the synthesis of novel substituted thieno[2,3-d]pyrimidine-4-carboxylic acids, their derivatization, and antimicrobial activity. Chem Heterocycl Comp 55, 184–188 (2019). https://doi.org/10.1007/s10593-019-02437-1

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  • DOI: https://doi.org/10.1007/s10593-019-02437-1

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