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Novel Benzyl‐ or 4‐Cyanobenzyl‐Substituted N‐Heterocyclic (Bromo)(carbene)silver(I) and (Carbene)(chloro)gold(I) Complexes: Synthesis and Preliminary Cytotoxicity Studies
Author(s) -
Patil Siddappa,
Deally Anthony,
Hackenberg Frauke,
Kaps Leonard,
MüllerBunz Helge,
Schobert Rainer,
Tacke Matthias
Publication year - 2011
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.201100107
Subject(s) - carbene , chemistry , bromide , benzyl bromide , transmetalation , medicinal chemistry , single crystal , silver oxide , crystallography , organic chemistry , catalysis
N‐Heterocyclic carbene (NHC) complexes bromo(1,3‐dibenzyl‐1,3‐dihydro‐2 H ‐imidazol‐2‐ylidene)silver(I) ( 2a ), bromo[1‐(4‐cyanobenzyl)‐3‐methyl‐1,3‐dihydro‐2 H ‐imidazol‐2‐ylidene]silver(I) ( 2b ), and bromo[1‐(4‐cyanobenzyl)‐3‐methyl‐1,3‐dihydro‐2 H ‐benzimidazol‐2‐ylidene]silver(I) ( 2c ) were prepared by the reaction of 1,3‐dibenzyl‐1 H ‐imidazol‐3‐ium bromide ( 1a ), 3‐(4‐cyanobenzyl)‐1‐methyl‐1 H ‐imidazol‐3‐ium bromide ( 1b ), and 3‐(4‐cyanobenzyl)‐1‐methyl‐1 H ‐benzimidazol‐3‐ium bromide ( 1c ), respectively, with silver(I) oxide. NHC Complexes chloro(1,3‐dibenzyl‐1,3‐dihydro‐2 H ‐imidazol‐2‐ylidene)gold(I) ( 3a ), chloro[1‐(4‐cyanobenzyl)‐3‐methyl‐1,3‐dihydro‐2 H ‐imidazol‐2‐ylidene]gold(I) ( 3b ), and chloro[1‐(4‐cyanobenzyl)‐3‐methyl‐1,3‐dihydro‐2 H ‐benzimidazol‐2‐ylidene]gold(I) ( 3c ) were prepared via transmetallation of corresponding (bromo)(NHC)silver(I) complexes with chloro(dimethylsulfido)gold(I). The complex 3a was characterized in two polymorphic forms by single‐crystal X‐ray diffraction showing two rotamers in the solid state. The cytotoxicities of all three bromo(NHC)silver(I) complexes and three (chloro)(NHC)gold(I) complexes were investigated through 3‐(4,5‐dimethylthiazol‐2‐yl)‐2,5‐diphenyl‐2 H ‐tetrazolium bormide (MTT)‐based preliminary in vitro testing on the Caki‐1 cell line in order to determine their IC 50 values. (Bromo)(NHC)silver(I) complexes 2a – 2c and (chloro)(NHC)gold(I) complexes 3a – 3c were found to have IC 50 values of 27±2, 28±2, 34±6, 10±1, 12±5, and 12±3 μ M , respectively, on the Caki‐1 cell line.