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Synthesis of 1-ethyl-1H-2,1-benzothiazine 2,2-dioxide derivatives using cycloalkanecarbaldehydes and evaluation of their antimicrobial activity

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Chemistry of Heterocyclic Compounds Aims and scope

4,6-Dihydropyrano[3,2-c][2,1]benzothiazine 5,5-dioxides were synthesized via three-component interaction of 1-ethyl-1H-2,1-benzothiazin-4(3H)-one 2,2-dioxide with active methylene nitriles and cycloalkanecarbaldehydes. The latter were also applied to obtain ammonium salts of 3,3'-(cycloalkylmethanediyl)bis(1-ethyl-1H-2,1-benzothiazin-4-ol) 2,2,2',2'-tetraoxides. The structures of the synthesized compounds were confirmed by 1H, 13C NMR as well as mass spectral and elemental analysis data. The structures of two representatives from each class of the target compounds have been additionally confirmed by single crystal X-ray diffraction study. The synthesized compounds were screened for antibacterial and antifungal activities.

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We would like to express our sincere gratitude to prof. Nataliya I. Filimonova and to Ms. Elena V. Kirshenbaum(Department of Microbiology, Virology and Immunology,National University of Pharmacy, Kharkiv) for theirassistance in antimicrobial studies.

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Authors and Affiliations

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

    Dmitry A. Lega, Valentine P. Chernykh & Leonid A. Shemchuk

  2. Pharmaceutical Faculty, Poznan University of Medical Sciences, 6 Grunwaldzka St., Poznan, 60780, Poland

    Lucjusz Zaprutko & Andrzej K. Gzella

Authors
  1. Dmitry A. Lega
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  2. Valentine P. Chernykh
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  3. Lucjusz Zaprutko
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  4. Andrzej K. Gzella
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  5. Leonid A. Shemchuk
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Correspondence to Leonid A. Shemchuk.

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Published in Khimiya Geterotsiklicheskikh Soedinenii, 2017, 53(2), 219–229

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Lega, D.A., Chernykh, V.P., Zaprutko, L. et al. Synthesis of 1-ethyl-1H-2,1-benzothiazine 2,2-dioxide derivatives using cycloalkanecarbaldehydes and evaluation of their antimicrobial activity. Chem Heterocycl Comp 53, 219–229 (2017). https://doi.org/10.1007/s10593-017-2043-7

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