Silyl modification of biologically active compounds. 11. Synthesis, physico-chemical and biological evaluation of N-(trialkoxysilylalkyl)tetrahydro(iso,silaiso) quinoline derivatives
✍ Scribed by Alla Zablotskaya; Izolda Segal; Sergey Belyakov; Edmunds Lukevics
- Publisher
- John Wiley and Sons
- Year
- 2005
- Tongue
- English
- Weight
- 135 KB
- Volume
- 20
- Category
- Article
- ISSN
- 0268-2605
- DOI
- 10.1002/aoc.1014
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✦ Synopsis
Abstract
N‐(trialkoxysilylalkyl) derivatives of 1,2,3,4‐tetrahydroquinoline, 1,2,3,4‐tetrahydroisoquinoline and 4,4‐dimethyl‐4‐sila‐1,2,3,4‐tetrahydroisoquinoline were prepared and characterized by elemental analysis, ^1^H, ^13^C and ^29^Si NMR spectroscopy. In vivo psychotropic properties and in vitro cytotoxic effects of 3‐[N‐(1,2,3,4‐tetrahydroisoquinolyl)]propyltriethoxysilane methiodide and 3‐[N‐(1,2,3,4‐tetrahydroisoquinolyl)]propylsilatrane are reported. Comparative study of ^29^Si shifts in newly synthesized compounds suggested donor–acceptor interaction between nitrogen and silicon atom, which increased electron density at Si nuclei, revealing a stronger increment of N → Si transannular bond in comparison with N → Si α‐effect. The molecular structure of 3‐[N‐(1,2,3,4‐tetrahydroisoquinolyl)]propylsilatrane features a penta‐coordinate silicon atom having CSiO~3~ pattern and Si…N intramolecular interaction. Copyright © 2005 John Wiley & Sons, Ltd.