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Synthesis and Antimicrobial Properties of Chiral Mannich Bases Containing a Norbornene Fragment

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Abstract

New Mannich bases were synthesized from chiral norbornenylmethanol, secondary amines, and formaldehyde. Their structure was confirmed by elemental analyses and IR, 1H and 13C NMR, and mass spectra. The products were optically active (dextrorotatory), and they showed high antimicrobial activity against Staphylococcus aureus, Klebsiella pneumoniae, Escherichia coli, and yeast-like fungi of the family Candida, which exceeded the activity of some drugs currently used in medical paractice. Minimum inhibitory and minimum bactericidal concentrations of the synthesized compounds were determined.

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ACKNOWLEDGMENTS

The authors thank their colleagues for their help in performing experiments, the staff of the Analytical Laboratory (for studying physicochemical properties of the synthesized compounds), the staff of the Pharmaceutical Chemistry Department (for measuring the optical rotations), and the staff of the Microbiology and Immunology Department (for studying antimicrobial activity) of the Azerbaijan Medical University. Special thanks to the Editorial Board of the journal (for help in the edition and publication of the article).

The synthesis of compounds was carried out at the Mamedaliev Institute of Petrochemical Processes, National Academy of Sciences of Azerbaijan.

Funding

This study was performed in the framework of contract no. 1/18 (April 12, 2018) on scientific and technical collaboration between the Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, and Mamedaliev Institute of Petrochemical Processes, National Academy of Sciences of Azerbaijan. The study was funded from the state budget.

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Authors and Affiliations

  1. Institute of Petrochemical Processes, National Academy of Sciences of Azerbaijan, 1025, Baku, Azerbaijan

    E. H. Mammadbayli, G. E. Hajieva & S. V. Ismayilova

  2. Azerbaijan State University of Oil and Industry, 1010, Baku, Azerbaijan

    L. M. Maharramova

Authors
  1. E. H. Mammadbayli
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  2. G. E. Hajieva
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  3. S. V. Ismayilova
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  4. L. M. Maharramova
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Corresponding author

Correspondence to E. H. Mammadbayli.

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The authors declare no conflict of interest.

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Translated from Zhurnal Organicheskoi Khimii, 2021, Vol. 57, No. 6, pp. 860–867 https://doi.org/10.31857/S0514749221060082.

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Mammadbayli, E.H., Hajieva, G.E., Ismayilova, S.V. et al. Synthesis and Antimicrobial Properties of Chiral Mannich Bases Containing a Norbornene Fragment. Russ J Org Chem 57, 936–941 (2021). https://doi.org/10.1134/S1070428021060087

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