The Search for Biologically Active Compounds in the Series of N-ethoxyethylpiperidine Derivatives

  • U. B. Issayeva Institute of Chemical Sciences named after A.B. Bekturov”, 050010, Ualikhanov str., 106, Almaty, Kazakhstan; National Medical University”, 050012, Tole bi str., 88, Almaty, Kazakhstan
  • G. S. Akhmetova Institute of Chemical Sciences named after A.B. Bekturov”, 050010, Ualikhanov str., 106, Almaty, Kazakhstan
  • U. M. Datkhayev National Medical University”, 050012, Tole bi str., 88, Almaty, Kazakhstan
  • M. T. Omyrzakov GxP Company, 050059/A15E2M1, Al-Farabi аve., 13 к1v, Almaty, Kazakhstan
  • K. D. Praliyev Institute of Chemical Sciences named after A.B. Bekturov”, 050010, Ualikhanov str., 106, Almaty, Kazakhstan
  • S. A. Ross National Medical University”, 050012, Tole bi str., 88, Almaty, Kazakhstan; National Center for Natural Products Research, School of Pharmacy, The University of Mississippi, University, MS 38677, USA; Department of Biomolecular Sciences, Division of Pharmacognosy, School of Pharmacy, The University of Mississippi, University, MS 38677, USA
Keywords: piperidine, ketoxime, piperidols, cyclopropane, para-, meta-, orthofluorobenzoates, antimicrobial activity

Abstract

With the aim to introduce fragment of cyclopropane and fragments of p-, m-, o-fluorophenyls into the structures of N-ethoxyethylpiperidines, acylation of oxime and phenylacetylenic alcohol of 1-(2-ethoxyethyl)-4-ketopiperidine by cyclopropanecarbonylchloride was carried out; on the basis of 1-(2-ethoxyethyl)-4-ethynyl-4-hydroxypiperidine (cascaine alcohol), acylation by 4-fluoro-, 3-fluoro-, 2-fluorobenzoylchlorides was carried out with formation of the corresponding piperidine containing hydrochlorides of cyclopropanecarboxylic acid esters and para-, meta-, ortho-fluorobenzoic esters. Acylation reaction on the hydroxyl group of compounds is carried out in absolute dioxane, the acylating agents are cyclopropanecarbonylchloride, p-, m-, o-fluorobenzoyl chlorides taken in excess. The obtained esters of cyclopropanecarboxylic and para-, meta-, ortho-fluorobenzoic acids are crystalline substances with a clear melting point, well soluble in water, ethanol, acetone. P-fluorobenzoates are obtained with better yields, m-fluorobenzoates occupy an intermediate position, and o-fluorobenzoates are formed with the lowest yields. The best yields of fluorobenzoates are obtained using dioxane as a solvent. Para-, meta-, ortho-fluorobenzoic esters of 1-(2-ethoxyethyl)-4-ethynyl-4-hydroxypiperidine coded A-4 – A-6 were studied for the presence of antimicrobial activity, the actions of these preparations were evaluated in vitro in relation to strains of gram-positive bacteria Staphylococcus aureus, Bacillus subtilis, gram-negative strains of Escheriсhia coli, Pseudomonas aeruginosa and to yeast fungus Сandida albicans by the diffusion method into agar (holes). Introduction of fluorine atom into the structure of cascaine lead to manifestation of antimicrobial activity.

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Published
2019-06-30
How to Cite
[1]
U. Issayeva, G. Akhmetova, U. Datkhayev, M. Omyrzakov, K. Praliyev, and S. Ross, “The Search for Biologically Active Compounds in the Series of N-ethoxyethylpiperidine Derivatives”, Eurasian Chem. Tech. J., vol. 21, no. 2, pp. 125-133, Jun. 2019.
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