Novel symmetrically p-benzyl-substituted 4,5-diaryl-imidazole N-heterocyclic carbene-silver(I) acetate complexes – Synthesis and biological evaluation

Novel derivatives of the antibiotic NHC–Ag(I) drug candidate SBC3: Synthesis, biological evaluation and 109Ag NMR studies

“…Crystal structures were obtained for all complexes 3-8 and structural information will be reviewed for any influence on the characteristic bonds observed in these types of NHC-silver(I) complexes. The g 2 -coordination between the silver(I) moiety and acetate oxygens are two and the possible argentophilic interactions are two notable phenomena that have previously been reported and were surveyed for in this work [15,[24][25][26][27][28].…”

“…In order to increase antibacterial ability, the transport of NHCsilver(I) complexes into bacterial cells is an important factor. The large derivability of imidazole-based NHCs [15,[24][25][26][27][28] allows for the incorporation of substituent groups that can bestow improved bioavailability and electronically influence the slow release of silver cations in the intracellular environment through the strong r-bonding of the NHC [13].…”

Novel Ruthenium(II) and Gold(I) NHC Complexes: Synthesis, Characterization, and Evaluation of Their Anticancer Properties

“…1 H NMR (400 MHz, CDCl 3 , δ ppm): 7.07 (d, J = 7.7 Hz, 4H, CH methylbenzyl + CH isopropylphenyl ), 6.90−6.62 (m, 12H, CH methylbenzyl + CH isopropylphenyl ), 6.27 (d, J = 17.2 Hz, 2H, CH cymene ), 5.23 (d, J = 5. 9 Hz, 2H, CH 2 ), 5.12 (m, 6H, CH 2 + CH cymene ), 2.71 (p, J = 6. 9 (1,3-Di(p-methylbenzyl)-4,5-di(p-methoxyphenyl)imidazol-2-ylidene](η 6 -p-cymene)ruthenium(II) Dichloride (5).…”

“…9 Hz, 2H, CH 2 ), 5.12 (m, 6H, CH 2 + CH cymene ), 2.71 (p, J = 6. 9 (1,3-Di(p-methylbenzyl)-4,5-di(p-methoxyphenyl)imidazol-2-ylidene](η 6 -p-cymene)ruthenium(II) Dichloride (5). 1,3-Di(p-methylbenzyl)-4,5-di(p-methoxyphenyl)imidazolium bromide 9 (228 mg, 0.400 mmol) and Ag 2 O (46 mg, 0.20 mmol) were stirred in 15 mL of dichloromethane in darkness at rt for 4 h. Dichloro(p-cymene)-ruthenium(II) dimer (122 mg, 0.200 mmol) was added, and the mixture was stirred for 4 h in darkness at rt.…”

“…1 H NMR (300 MHz, CDCl 3 , δ ppm): 7.02 (dd, J = 8.0 Hz, 8H, CH methylphenyl + CH methylbenzyl ), 6.93 (d, J = 8.1 Hz, 4H, CH methylphenyl + CH methylbenzyl ), 6.86 (d, J = 8.1 Hz, 4H, CH methylphenyl + CH methylbenzyl ), 5.34 (s, 4H, CH 2 ), 2.30 (s, 6H, CH 3methylphenyl ), 2.29 (s, 6H, CH 3methylbenzyl ). 13 (1,3-Di(p-methoxybenzyl)-4,5-di(p-isopropylphenyl)imidazol-2-ylidene)gold(I) Chloride (9). 1,3-Di(p-methoxybenzyl)-4,5-di(pisopropylphenyl)imidazolium chloride 20 (291 mg, 0.500 mmol) and Ag 2 O (56 mg, 0.28 mmol) were dissolved in 10 mL of dichloromethane and stirred for 4 h at rt in darkness.…”