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Synthesis, structure and biological activity of new 6,6‐dimethyl‐2‐oxo‐4‐{2‐[5‐organylsilyl(germyl)]furan(thiophen)‐2‐yl}vinyl‐5,6‐dihydro‐2 H ‐pyran‐3‐carbonitriles
Author(s) -
Ignatovich Luba,
Spura Jana,
Muravenko Velta,
Belyakov Sergey,
Popelis Juris,
Shestakova Irina,
Domrachova Ilona,
Gulbe Anita,
Rudevica Zhanna,
Leonchiks Ainars
Publication year - 2015
Publication title -
applied organometallic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.53
H-Index - 71
eISSN - 1099-0739
pISSN - 0268-2605
DOI - 10.1002/aoc.3363
Subject(s) - chemistry , pyran , trimethylsilyl , furan , substituent , piperidine , nuclear magnetic resonance spectroscopy , dihydropyran , catalysis , organic chemistry , medicinal chemistry
New 6,6‐dimethyl‐2‐oxo‐4‐{2‐[5‐alkylsilyl(germyl)]furan(thiophen)‐2‐yl}vinyl‐5,6‐dihydro‐2 H ‐pyran‐3‐carbonitriles (IC 50 : 1–6 µg ml −1 ) have been prepared by the condensation of corresponding silicon‐ and germanium‐containing furyl(thienyl)‐2‐carbaldehydes with 3‐cyano‐4,6,6‐trimethyl‐5,6‐dihydropyran‐2‐one using piperidine acetate as a catalyst. The obtained carbonitriles were identified using NMR ( 1 H, 13 C and 29 Si) spectroscopy and GC‐MS. The structure of 6,6‐dimethyl‐2‐oxo‐4‐[2‐(5‐trimethylsilyl)thiophen‐2‐yl]‐5,6‐dihydro‐2 H ‐pyran‐3‐carbonitrile was studied using X‐ray diffractometry. The influences of the heterocycle and the structure of the organoelement substituent on cytotoxicity and on matrix metalloproteinase inhibition have been studied. Copyright © 2015 John Wiley & Sons, Ltd.