Synthesis and biological properties of 1-(4-substituted phenyl)-1-alkyl(aryl)-2-phenyl-3-piperidinopropan-1-ols

Abstract

Interaction of a-phenyl-b-piperidino-4-substituted propiophenones with Grignard reagents in ether was used to synthesize 1-(4-substituted phenyl)-1-alkyl(aryl)-2-phenyl-3-piperidinopropan-1-ols. The antibacterial and antioxidant properties of the aminopropanol hydrochlorides were studied. Some of these compounds (3-(4-ethoxyphenyl)-2-phenyl-1-piperidinoheptan-, 3-(4-ethoxyphenyl)-2-phenyl-1-piperidonooctan-, and 2-phenyl-1-piperidino-3-(4-propoxyphenyl)decan-3-ol hydrochlorides) had moderate antibacterial activity and some (3-(4-ethoxyphenyl)-2-phenyl-1-piperidinopentan-and 3-(4-ethoxyphenyl)-5-methyl-2-phenyl-1-piperidinohexan-3-ol hydrochlorides) had high antioxidant activity.Extensive data on the biological properties of ternary aminopropanols synthesized by ourselves create the need for widening and deepening their study. In continuation of our previous reports [1-4] on the "structure-biological activity" relationships of cyclodol analogs (1-cyclohexyl-1-phenyl-3-piperidinopropan-1-ol hydrochlorides), interaction of b-aminoketones with a variety of Grignard reagents was used to prepare a new series of aminopropanols, II. We have previously demonstrated that tertiary aminopropanols have a variety of biological properties [5,6]. The aims of the present work were to synthesize 1-(4-substituted phenyl)-1-alkyl-(aryl)-2-phenyl-3-piperidinopropan-1-ols (II) in which the hydrogen atom of the keto group in the a position is substituted by a phenyl radical and the amine fragment is piperidine, and to study the biological properties of aminopropanol hydrochlorides III -XX.The b-piperidinopropiophenones (I) required for the synthesis were prepared as described in [7]. The biological properties of aminopropanols (II) were studied after conversion to the corresponding hydrochlorides (III-XX); the antibacterial and antioxidant activities of these compounds were assessed.The structures of the compounds synthesized were confirmed by IR and 1 H NMR spectroscopy. EXPERIMENTAL CHEMICAL SECTIONIR spectra were recorded on Specord 75-IR and FT-IR Nexus instruments and 1 H NMR spectra on a Mercury-300 224 0091-150X/11/4504-0224