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‐2H‐pyran‐3‐carbonitriles |
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| Authors: | Luba Ignatovich Jana Spura Velta Muravenko Sergey Belyakov Juris Popelis Irina Shestakova Ilona Domrachova Anita Gulbe Zhanna Rudevica Ainars Leonchiks |
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| Affiliation: | 1. Latvian Institute of Organic Synthesis, Riga, LV, Latvia;2. Latvian Biomedical Research and Study Centre, Riga, LV, Latvia |
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| Abstract: | New 6,6‐dimethyl‐2‐oxo‐4‐{2‐[5‐alkylsilyl(germyl)]furan(thiophen)‐2‐yl}vinyl‐5,6‐dihydro‐2H‐pyran‐3‐carbonitriles (IC50: 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 (1H, 13C and 29Si) spectroscopy and GC‐MS. The structure of 6,6‐dimethyl‐2‐oxo‐4‐[2‐(5‐trimethylsilyl)thiophen‐2‐yl]‐5,6‐dihydro‐2H‐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. |
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| Keywords: | silyl‐ and germyl(furyl)thienyl derivatives of 6,6‐dimethyl‐2‐oxo‐5,6‐dihydro‐2H‐pyran‐3‐carbonitrile synthesis X‐ray 1H NMR 13C NMR 29Si NMR cytotoxic activity toxicity MMP inhibition |
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