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

摘要

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 mu g 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 (H-1, C-13 and Si-29) 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 (c) 2015 John Wiley & Sons, Ltd.