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N‐Heterocyclic carbenes derived from imidazo‐[1,5‐ a ]pyridines related to natural products: synthesis, structure and potential biological activity of some corresponding gold(I) and silver(I) complexes
Author(s) -
Mihorianu Monica,
Franz M Heiko,
Jones Peter G,
Freytag Matthias,
Kelter Gerhard,
Fiebig HeinzHerbert,
Tamm Matthias,
Neda Ion
Publication year - 2016
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.3474
Subject(s) - chemistry , carbene , iodide , mass spectrometry , nuclear magnetic resonance spectroscopy , single crystal , stereochemistry , crystal structure , medicinal chemistry , crystallography , organic chemistry , catalysis , chromatography
A series of Au(I) complexes ( 12 , 13 , 14 , 15 , 16 ) and Ag(I) complexes ( 17 , 18 , 19 , 20 ) derived from imidazo[1,5‐ a ]pyridin‐3‐ylidenes were synthesized from AuCl(SMe 2 ) or by reacting silver(I) acetate with 2,5‐dimethylimidazo[1,5‐ a ]pyridin‐2‐ium iodide or imidazo[1,5‐ a ]pyridin‐2‐ium salts, and were characterized using NMR spectroscopy, mass spectrometry and elemental analyses. In addition, the Au(I) complex 13 and the Ag(I) complex 19 were characterized using single‐crystal X‐ray diffraction. Using paclitaxel as a standard, all Au(I) and Ag(I) N‐heterocyclic carbene complexes were evaluated for their in vitro anti‐tumour activity against 12 cell lines using a monolayer cell survival and proliferation assay. The highest anticancer activity was found for complexes 15 , 13 and 14 with mean IC 50 values of 10.09, 10.42 and 12.28 μM, respectively. Copyright © 2016 John Wiley & Sons, Ltd.