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A new 2-(4H-1,3-benzoxazin-4-on-2-yl)-1,3-tropolone: Synthesis, structure, and antibacterial properties

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Abstract

2-(4H-1,3-Benzoxazin-4-on-2-yl)-4,5,6-trichloro-1,3-tropolone, structural properties of which were studied using 1H NMR, IR-spectroscopy, mass spectrometry, and quantum chemistry has been obtained for the first time using an acid-catalyzed condensation reaction of 3,4,5,6-tetrachloro-1,2-benzoquinone with 2-methyl-4H-3,1-benzoxazin-4-one. It has been shown that the new tropolone possesses antibacterial activity against hospital-acquired strains of gram-negative (Escherichia coli, Salmonella enterica sv. Enteritidis, Acinetobacter baumannii, and Pseudomonas aeruginosa) and Gram-positive (Staphylococcus aureus) bacteria. The obtained substance is suggested for development of a new antibacterial drug.

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Authors and Affiliations

  1. Southern Scientific Center, Russian Academy of Sciences, ul. Chekhova 41, Rostov-on-Don, 344006, Russia

    Yu. A. Sayapin & V. I. Minkin

  2. Research Institute of Physical and Organic Chemistry, Southern State University, Rostov-on-Don, 344090, Russia

    E. A. Gusakov, I. V. Dorogan, I. O. Tupaeva & V. I. Minkin

  3. State Scientific Center of Applied Microbiology and Biotechnology, Obolensk, Moscow oblast, 142279, Russia

    M. G. Teimurazov, N. K. Fursova & K. V. Ovchinnikov

Authors
  1. Yu. A. Sayapin
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  2. E. A. Gusakov
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  3. I. V. Dorogan
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  4. I. O. Tupaeva
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  5. M. G. Teimurazov
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  6. N. K. Fursova
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  7. K. V. Ovchinnikov
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  8. V. I. Minkin
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Corresponding author

Correspondence to Yu. A. Sayapin.

Additional information

Original Russian Text © Yu.A. Sayapin, E.A. Gusakov, I.V. Dorogan, I.O. Tupaeva, M.G. Teimurazov, N.K. Fursova, K.V. Ovchinnikov, V.I. Minkin, 2016, published in Bioorganicheskaya Khimiya, 2016, Vol. 42, No. 2, pp. 247–252.

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Sayapin, Y.A., Gusakov, E.A., Dorogan, I.V. et al. A new 2-(4H-1,3-benzoxazin-4-on-2-yl)-1,3-tropolone: Synthesis, structure, and antibacterial properties. Russ J Bioorg Chem 42, 224–228 (2016). https://doi.org/10.1134/S1068162016020114

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  • DOI: https://doi.org/10.1134/S1068162016020114

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