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Synthesis and Antimicrobial Activity of Cyclohexane-Containing Mannich Bases Derived from Secondary Amines

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Abstract

New Mannich bases were synthesized from cyclohexanol, formaldehyde, and secondary amines such as piperidine, morpholine, azepane, diethylamine, dipropylamine, dibutylamine, and dihexylamine. The reactions were carried out with equimolar amounts of the reactants in benzene at 78–80°C for 4–5 h, and the yields ranged from 63 to 80%. The synthesized compounds were characterized by physical constants, IR, 1H and 13C NMR, and mass spectra, and elemental analyses. Their antimicrobial activity was evaluated against gram-positive and gram-negative bacteria (S. aureus, E. coli, P. aeruginosa, K. pneumoniae) and yeast-like fungus of the genus Candida. The results of antimicrobial screening made it possible to recommend the obtained Mannich bases for the design of new antimicrobial agents.

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ACKNOWLEDGMENTS

The authors thank their colleagues for their help in carrying out experiments, the staff of the analytical laboratory for studying physicochemical properties of the synthesized compounds, and the staff of the Microbiology and Immunology Department of the Azerbaijan Medical University for performing antimicrobial evaluation, and also specially thank the reviewers and Editorial staff of the journal for their help in editing and publishing the manuscript. The syntheses were carried out at the Mamedaliev Institute of Petrochemical Processes, National Academy of Sciences of Azerbaijan. The antimicrobial activity of the synthesized compounds was studied at the Azerbaijan Medical University. The mass spectra and NMR spectra of some compounds were recorded at the Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences.

Funding

This study was performed according to Agreement no. 1/18, April 12, 2018, on scientific and technical collabo­ra­tion between Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, and Mamedaliev Institute of Petrochemical Processes, National Academy of Sciences of Azerbaijan, and was financially supported by the state budget.

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Authors and Affiliations

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

    E. H. Mammadbayli, S. V. Ismayilova & G. A. Hajiyeva

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

    N. A. Jafarova & E. I. Suleymanova

Authors
  1. E. H. Mammadbayli
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  2. S. V. Ismayilova
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  3. G. A. Hajiyeva
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  4. N. A. Jafarova
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  5. E. I. Suleymanova
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Corresponding author

Correspondence to E. H. Mammadbayli.

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The authors declare the absence of conflict of interest.

Additional information

Translated from Zhurnal Organicheskoi Khimii, 2022, Vol. 58, No. 10, pp. 1088–1095 https://doi.org/10.31857/S0514749222100068.

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Mammadbayli, E.H., Ismayilova, S.V., Hajiyeva, G.A. et al. Synthesis and Antimicrobial Activity of Cyclohexane-Containing Mannich Bases Derived from Secondary Amines. Russ J Org Chem 58, 1423–1428 (2022). https://doi.org/10.1134/S1070428022100062

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