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

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 1H, 13C and 29Si 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. Copyright (c) 2012 John Wiley & Sons, Ltd.