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 |
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| Authors: | Alla Zablotskaya Izolda Segal Yuris Popelis Solveiga Grinberga Irina Shestakova Vizma Nikolajeva Daina Eze |
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| Institution: | 1. Latvian Institute of Organic Synthesis, , Riga, LV‐1006 Latvia;2. Biological Faculty, University of Latvia, , Riga, LV‐1586 Latvia |
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| 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 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 © 2012 John Wiley & Sons, Ltd. |
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| Keywords: | silicon silylation choline drug research tetrahydro(iso)quinoline antitumour activity antimicrobial activity |
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