Synthesis and properties of aminomethoxy 1-(benzylsulfanyl)octane-2-ol derivatives

Abstract

A previously unknown sulfur-containing alcohol, 1-(benzylsulfanyl)octane-2-ol, was synthesized in 65% yield. Further, on the basis of the obtained alcohol, formaldehyde, and aliphatic (diethyl-, dibutyl-, dipropyl-, dipentyl-, dihexylamine) or heterocyclic (piperidine, morpholine, hexamethyleneimine) amines, new representatives of 2-aminomethoxy derivatives of 1-(benzylsulfanyl)octane-2-ol were obtained by Mannich condensation. The yield of target products was 68-75%. The physicochemical data of the synthesized compounds were determined. The composition and structure of the obtained compounds were confirmed by elemental analysis, IR, 1H NMR spectroscopy, and mass spectrometry. The resulting products are colorless liquids with a characteristic odor, insoluble in water, and readily soluble in organic solvents. The synthesized compounds were tested for antimicrobial activity against pathogenic and conditionally pathogenic microorganisms. The antimicrobial activity of the substances was studied by the method of serial dilutions. The results obtained showed that the tested compounds exhibit more pronounced antimicrobial activity than alcohol, carbolic acid (phenol), rivanol, nitrofungin, furacillin and chloramine used in practice. The synthesized compounds have also been tested as antimicrobial additives to oils, and it has been found that they effectively suppress the vital activity of microorganisms.