1051373-76-2Relevant academic research and scientific papers
Synthesis and biological evaluation of novel imidazole-containing macrocycles
Nshimyumukiza, Prosper,Van Den Berge, Emilie,Delest, Bruno,Mijatovic, Tatjana,Kiss, Robert,Marchand-Brynaert, Jacqueline,Robiette, Rapha?l
, p. 4515 - 4520 (2010/07/09)
A new family of compounds made of a 5-aryl-1H-imidazole motif included in a macrocycle has been designed and synthesized. The synthesis of the imidazole core makes use of our previously developed method for the regioselective preparation of 1,2,5-trisubstituted imidazoles while the construction of the macrocycle is based on a three steps sequence: SNAr, Suzuki coupling, and RCM reaction. Biological evaluation of synthesized imidazole-containing macrocycles revealed that they display actual binding activity toward A3 adenosine (h) receptor, dopamine D1 (h) receptor, chloride channel (GABA-gated), and choline transporter (h) CHT1.
Divergent and regioselective synthesis of 1,2,4- and 1,2,5-trisubstituted imidazoles
Delest, Bruno,Nshimyumukiza, Prosper,Fasbender, Olivier,Tinant, Bernard,Marchand-Brynaert, Jacqueline,Darro, Francis,Robiette, Raphael
, p. 6816 - 6823 (2008/12/22)
(Chemical Equation Presented) A divergent and regioselective synthesis of 1,2,4- and 1,2,5-trisubstituted imidazoles from a readily available (two steps) common intermediate has been developed. This methodology is based on the regiocontrolled N-alkylation of 1-(N,N-dimethylsulfamoyl)-5-iodo-2-phenylthio- 1H-imidazole (10). When this intermediate is engaged in reaction with methyl triflate, selective formation of the corresponding 1,2,5-trisubsituted 1H-imidazole is observed. NMR studies have revealed that this regioselectivity can be accounted for by in situ rapid isomerization of 10 into its 1,2,4-isomer (13) followed by regiospecific N-alkylation of the latter. Conversely, when key intermediate 10 is slowly added to Meerwein's salt, isomerization can be constrained and regiospecific N-alkylation of 10 leads to 1,2,4-trisubstituted 1H-imidazole with a high selectivity. The general character of this methodology has been illustrated by showing that iodine in position 4 or 5 could be easily substituted by an aryl group by Suzuki coupling, whereas the phenylthio group at position 2 could, after oxidation into sulfone, be displaced by nucleophilic substitution.
