Silyl modification of biologically active compounds. 13. Synthesis, cytotoxicity and antibacterial action of N‐methyl‐N‐(2‐triorganylsiloxyethyl)‐1,2,3,4‐tetrahydro(iso)quinolinium iodides

Abstract

A series of N-methyl-N-(2-triorganylsiloxyethyl)-1,2,3,4-tetrahydro(iso)quinolinium iodides has been synthesized via dehydrocondensation reaction of N-(2-hydroxyethyl)-1,2,3,4-tetrahydroisoquinoline, N-(2-hydroxyethyl)-1,2,3,4-tetrahydroquinoline and 4,4-dimethyl-N-(2-hydroxyethyl)-4-sila-1,2,3,4-tetrahydroisoquinoline with trialkyl(aryl)hydrosilanes and subsequent alkylation, and characterized by 1 H, 13 C and 29 Si NMR and mass spectroscopy. The biological activity data exhibited a marked enhancement of inhibitory activity against tumour cell lines and almost all the test bacterial/fungal strains in comparison with their 2-hydroxyethyl precursors. Cytotoxicity in the microgram range against HT-1080 (human fibrosarcoma) and MG-22A (mouse hepatoma) cancer cell lines was observed for most of compounds.

Iron oxide superparamagnetic nanocarriers bearing amphiphilic N‐heterocyclic choline analogues as potential antimicrobial agents

“…Intermediate 1 was synthesized from the commercially available materials 1,2,3,4‐tetrahydroisoquinoline and ethylene bromohydrin according to a method previously described and was modified by introduction of undecyl substituent by alkylation of either side chain or heterocyclic nitrogen atom with 1‐iodoundecane to provide the products of O ‐alkylation ( 3 ) and N ‐alkylation ( 4 ). Ether 2 was also converted to O , N ‐bis‐undecyl‐substituted tetrahydroisoquinolinium derivative 5 .…”

“…N ‐(2‐Hydroxyethyl)‐1,2,3,4‐tetrahydroisoquinoline ( 1 ) was characterized by comparing its 1 H NMR spectrum with those reported in the literature.…”

Superparamagnetic iron oxide/oleic acid nanoparticles with immobilized organosilicon derivatives of N‐(2‐hydroxyethyl)tetrahydroisoquinoline: synthesis, morphology and interaction with normal and tumour cells

“…N ‐(2‐Hydroxyethyl)‐1,2,3,4‐tetrahydroisoquinoline ( 1 ), N ‐(2‐ n ‐decyldimethylsiloxyethyl)‐1,2,3,4‐tetrahydroisoquinoline ( 2 ), N ‐(2‐dimethyl‐ n ‐hexadecylsiloxyethyl)‐1,2,3,4‐tetrahidroisoquinoline ( 3 ), N ‐(2‐ n ‐decyldimethylsiloxyethyl)‐ N ‐methyl‐1,2,3,4‐tetrahydroisoquinolinium iodide ( 4 ) and N ‐(2‐dimethyl‐ n ‐hexadecylsiloxyethyl)‐ N ‐methyl‐1,2,3,4‐tetrahydroisoquinolinium iodide ( 5 ) were obtained following procedures described in the literature …”

“…(4) and N-(2-dimethyl-n-hexadecylsiloxyethyl)-N-methyl-1,2,3,4-tetrahydroisoquinolinium iodide (5) were obtained following procedures described in the literature. [25] Synthesis of Nanoparticles Magnetite particles (Fe 3 O 4 ) 6 were obtained by wet synthesis by precipitation from an aqueous solution of Fe(II) sulphate and Fe(III) chloride with excess amount of sodium hydroxide. Initial toluene-based magnetic fluids 7.1 and 7.2 were synthesized by coating of magnetic particles with OA as surfactant according to the described procedure [26] and differed by their content.…”

“…[25] Silylated N-heterocyclic choline and colamine analogues, namely N-(2-siloxyethyl)-1,2,3,4-tetrahydroisoquinoline derivatives 2-5, possessed the same organosilicon substituents (decyldimethyland dimethylhexadecyl-), which proved to be optimal ones in the study of the most effective magnetic fluids obtained from their aliphatic analogues. [30] A methodological approach allowing preparation of aqueous magnetic colloids for biological investigation has been developed and includes the following stages: synthesis of lipid like À ) from the initial magnetic fluid; samples 11 and 12 were further used to produce corresponding aqueous magnetic solutions 13 and 14 and water-soluble powders 15 and 16.…”