Molbank (Jul 2023)

<i>N</i>-(((1<i>S</i>,5<i>R</i>)-6,6-Dimethylbicyclo[3.1.1]hept-2-en-2-yl)methyl)-3-dodecan/tetradecanamido-<i>N</i>,<i>N</i>-dimethylpropan-1-aminium Bromide

  • Liliya E. Nikitina,
  • Ilmir R. Gilfanov,
  • Roman S. Pavelyev,
  • Svetlana A. Lisovskaya,
  • Elena Y. Trizna,
  • Ilfat Z. Rakhmatullin,
  • Vladimir V. Klochkov,
  • Rustam R. Davletshin,
  • Olga B. Babaeva,
  • Alena I. Kolesnikova,
  • Olga V. Ostolopovskaya,
  • Larisa L. Frolova,
  • Airat R. Kayumov

DOI
https://doi.org/10.3390/M1704
Journal volume & issue
Vol. 2023, no. 3
p. M1704

Abstract

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The syntheses of the title compounds were performed using lauric and myristic acids. The compounds obtained were characterized using 1H-, 13C-NMR and 2D 1H-1H COSY, 1H-13C HSQC NMR, IR, and high-resolution mass spectrometry. Both compounds exhibited bactericidal activity on S. aureus comparable to that of a reference drug (miramistin). Compound 10, with lauric acid fragment, had a 16-fold higher activity on P. aeruginosa compared to compound 11, which in turn contains myristic acid fragment (with minimum inhibitory concentrations of 32 and 512 μg/mL, respectively). Compound 11 exhibited a pronounced activity against all types of fungi (higher than the activity of miramistin), while the activity of compound 10 was considerably lower. Thus, compound 11 can serve as a promising antimicrobial agent for the treatment of various fungal and staphylococcal infections, while compound 10 is of interest to treat P. aeruginosa-associated infections.

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