SYNTHESIS OF 1-(1H-IMIDAZOL-2-YL)ETHANE-1,2-DIOL DERIVATIVES - A NOVEL CLASS OF PROTEIN-KINASE-C INHIBITORS

Compounds 6-13 were prepared starting from 1-(triphenlymethyl)-protect ed 1H-imidazoles 14 and 15 in several steps. Lithiation with BuLi in T HF followed by reaction with (triphenylmethoxy)acetaldehyde (16) affor ded 17 and 18, respectively. O-Methylation of 17 and 18 gave diethers 19 and 20, respectively. The N- and O-trityl protecting groups of 17-2 0 were cleaved by acid treatment to give deprotected compounds 21-24. Acylation with equimolar amounts (for mono- or di-O-acylation) of the corresponding acyl chlorides yielded 1H-imidazoles 6-13. Compounds 7, 8, 10, and 11 exhibited moderate protein kinase C inhibition.