1214247-91-2Relevant academic research and scientific papers
Synthesis of imidazole derivatives with antimycobacterial activity
Miranda, Pedro O.,Gundersen, Lise-Lotte
experimental part, p. 40 - 47 (2010/06/13)
4-Substituted 1-(p-methoxybenzyl)imidazoles were designed and synthesized in order to mimic parts of the structure of highly potent antimycobacterial 6-aryl-9-(p-methoxybenzyl)purines. 4-Haloimidazoles were subjected to Pd-catalyzed cross-coupling in order to introduce a (hetero)-aryl group, or they were converted to Grignard reagents and reacted with (hetero)arylaldehydes. Further transformations of the adducts gave a variety of potential antimycobacterials with different "spacers" between the imidazole and (hetero)aryl group. The adduct from furfural was rearranged to a cyclopentenone derivative when treated with methanol under acidic conditions. Several target compounds exhibited antimycobacterial activity in vitro (IC90 13 μg/mL for the best inhibitors), but they were not as active as the most potent purines and pyrimidines synthesized before.
