Biopolym. Cell. 2019; 35(5):349-355.
Bioorganic Chemistry
Investigation of Antimicrobial Activity of 1,3-benzoxazine Derivatives
1Zahorulko S. P., 1Varenichenko S. A., 2Farat O. K., 3Markova I. V., 1Markov V. I.
  1. Ukrainian State University of Chemical Technology
    8 Gagarina Ave., Dnipro, Ukraine, 49005
  2. M. V. Lomonosov Moscow State University
    Leninskie Gory, 1/12, Moscow, Russian Federation, 119991
  3. Dnipro National University of Railway Transport named after V. Lazaryana
    2, Lazaryan Str., Dnipro, Ukraine, 49010

Abstract

Aim. To investigate potential antimicrobial activity of 1,3-benzoxazines derivatives. Methods. Synthesis, antimicrobial screening, antimicrobial and antifungal activity testing in vitro. Results. For antimicrobial screening, we chose the compounds that differed from the investigated ones by 30 %. Five compounds were selected and their antimicrobial activity against five bacterium and two fungus strains was studied by the methods of microbial growth inhibition assay. The percentage of growth inhibition of an individual sample is calculated considering a negative control (media only) and a positive control (bacterial / fungal media without inhibitors). The results obtained showed that compounds 2-[5-(4-nitrophenyl)-1H-pyrazol-3-yl]phenol and 6,8-diisopropylspiro[1,3-benzoxazine-2,1’-cyclohexan]-4(3H)-one in concentration of 32 μg/ml have the highest activity against Acinetobacter baumannii - 43 % and 27 %, respectively. The compound, 6,8-diisopropyl-2-methyl-2-(4-nitrophenyl)-2,3-dihydro-4H-1,3-benzoxazine-4-one showed the fungicidal activity against the Candida albicans strain. Conclusion. The derivatives of 1,3-benzoxazines exhibit a moderate antimicrobial activity, which allows the recommendation to continue the search for effective antimicrobials among the chemical compounds of this group, in particular, through the targeted synthesis of new compounds with predicted antimicrobial properties.
Keywords: 1,3-benzoxazines, 1H-pyrazol-3-yl-phenol, antimicrobial screening

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