220480-63-7

Upstream product

• 79487-95-9 1-methyl-2-phenylsulfanyl-1H-imidazole 
• 882-33-7 diphenyldisulfane 
• 1051373-75-1 5-iodo-2-phenylthio-1H-imidazole 
• 74-88-4 methyl iodide 
• 1051373-76-2 1-(N,N-dimethylsulfamoyl)-5-iodo-2-phenylthio-1H-imidazole 
• 420-37-1 trimethoxonium tetrafluoroborate 
• 77-78-1 dimethyl sulfate 
• 333-27-7 methyl trifluoromethanesulfonate 
• 1051373-80-8 CF₃O₃S^(1-)*C₁₂H₁₅IN₃O₂S₂⁽¹⁺⁾ 

Downstream Products

• 345349-05-5 5-iodo-1-methyl-2-phenylsulfonyl-1H-imidazole 
• 569643-22-7 5-(1-methoxy-1H-indol-2-yl)-1-methyl-2-phenylthio-1H-imidazole 
• 569643-23-8 5-(1H-indol-2-yl)-1-methyl-2-phenylthio-1H-imidazole 
• 569643-24-9 3-bromo-4-[2-(1-methyl-2-phenylthio-1H-imidazol-5-yl)-1H-indol-3-yl]-1-methyl-pyrrole-2,5-dione 
• 569643-26-1 3-bromo-4-[2-(1-methyl-2-phenylthio-1H-imidazol-5-yl)-1H-indol-3-yl]-pyrrole-2,5-dione 
• 345349-06-6 2-benzenesulfonyl-1-methyl-5-phenyl-1H-imidazole 
• 1448857-92-8 C₂₂H₂₄N₂O₃S 

Relevant academic research and scientific papers

Development of a regioselective N-methylation of (benz)imidazoles providing the more sterically hindered isomer

An efficient and highly regioselective N-methylation of (NH)-(benz)imidazoles furnishing the sterically more hindered, less stable, and usually minor regioisomer has been developed. The methodology involves very mild reaction conditions and tolerates a wide range of functional groups.

Synthesis and biological evaluation of novel imidazole-containing macrocycles

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

(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.

3-‘4-HETEROCYCLYL -1,2,3,-TRIAZOL-1-YL!-N-ARYL-BENZAMIDES AS INHIBITORS OF THE CYTOKINES PRODUCTION FOR THE TREATMENT OF CHRONIC INFLAMMATORY DISEASES

Disclosed compounds of formula (I), which inhibit production of cytokines involved in inflammatory processes and are thus useful for treating diseases and pathological conditions involving inflammation such as chronic inflammatory disease. Also disclosed are processes for preparing these compounds and pharmaceutical compositions comprising these compounds.

Parallel synthesis and evaluation of N-(1-phenylethyl)-5-phenyl-imidazole-2-amines as Na+/K+ ATPase inhibitors

A series of N-(1-phenylethyl)-5-phenyl-imidazole-2-amines was prepared using solution-phase, parallel synthesis and evaluated for Na+/K+ ATPase inhibition. (C) 2000 Elsevier Science Ltd. All rights reserved.

Introduction of alkenyl group bearing an electron-withdrawing group to the 5-position of imidazole ring by heck reaction

A DMF solution of 5-iodo-1-methyl-2-phenylthio-1H-imidazole (7) and a large excess of acrylic esters, acrylonitrile, or methyl vinyl ketone was heated in a sealed tube in the presence of Pd(PPh3)4 to give the Heck reaction products,