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Synthesis and Properties of Aminomethoxy Derivatives of 1-(Benzylsulfanyl)octan-2-ol

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Abstract

Previously unknown sulfur-containing alcohol, 1-(benzylsulfanyl)octan-2-ol, was synthesized in 65% yield and involved in the Mannich condensation with formaldehyde and aliphatic (diethyl-, dibutyl-, dipropyl-, dipentyl-, dihexylamine) or cyclic (piperidine, morpholine, hexamethyleneimine) secondary amines, which afforded new [1-(benzylsulfanyl)octan-2-yloxy]methanamines in 68–75% yields. The products were characterized by physical constants, and their structure was confirmed by elemental analyses and IR, 1H NMR, and mass spectra. They were isolated as colorless liquids with a characteristic odor, which are insoluble in water and readily soluble in organic solvents. The synthesized compounds were screened for antimicrobial activity against pathogenic and conditionally pathogenic microorganisms by the serial dilution method. The tested compounds proved to be more potent than medically used ethanol, phenol, ethacridine lactate, nitrofungin, nitrofurazone, and chloramine. The synthesized compounds were also tested as antimicrobial oil additives and were found to effectively inhibit the growth of Aspergillus niger, Candida tropicalis, Mycobacterium lacticola, and Pseudomonas aeruginosa.

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ACKNOWLEDGMENTS

The authors thank their colleagues for their help in performing experiments, the staff of the analytical laboratiry for studying physicochemical properties of the synthesized compounds, and the staffs of the Microbiology and Immunology Department (Azerbaijan Medical University) and the Institute of the Chemistry of Additives (National Academy of Sciences of Azerbaijan) for studying antimicro­bial activity of the synthesized compounds. Special thanks to the reviewers and Editorial Board of the journal for their help in editing and publishing the manuscript.

Funding

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

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Authors and Affiliations

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

    E. H. Mammadbayli

  2. Azerbaijan State Pedagogical University, 1000, Baku, Azerbaijan

    I. A. Jafarov & A. D. Astanova

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

    A. G. Shakhmammadova & A. G. Habibova

Authors
  1. E. H. Mammadbayli
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  2. I. A. Jafarov
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  3. A. D. Astanova
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  4. A. G. Shakhmammadova
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  5. A. G. Habibova
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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, 2023, Vol. 59, No. 1, pp. 89–96 https://doi.org/10.31857/S051474922301007X.

Dedicated to the blessed memory of the famous urologist Sohrab Huseingulu Oglu Mammedov

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Mammadbayli, E.H., Jafarov, I.A., Astanova, A.D. et al. Synthesis and Properties of Aminomethoxy Derivatives of 1-(Benzylsulfanyl)octan-2-ol. Russ J Org Chem 59, 54–59 (2023). https://doi.org/10.1134/S1070428023010050

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