Heme oxygenase inhibition by 2-oxy-substituted 1-(1H-imidazol-1-yl)-4-phenylbutanes: Effect of halogen substitution in the phenyl ring
Journal Publication ResearchOnline@JCUAbstract
A series of 2-oxy-substituted 1-(1H-imidazol-1-yl)-4-phenylbutanes comprising imidazole–ketones, imidazole–dioxolanes, and imidazole–alcohols substituted with halogens in the phenyl ring were synthesized and evaluated as novel inhibitors of heme oxygenase which are structurally distinct from metalloporphyrins. The entire library of compounds was found to be highly active, with the bromine- and iodine-substituted derivatives being the most potent. The imidazole–dioxolanes were all selective for the HO-1 isozyme (inducible) and exhibited substantially lower activity toward the HO-2 isozyme (constitutive). The corresponding imidazole–ketones and imidazole–alcohols showed selectivity toward HO-1 to a lesser degree than the similarly substituted imidazole–dioxolanes.
Journal
BIOORGANIC & MEDICINAL CHEMISTRY
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Volume
15
ISBN/ISSN
1464-3391
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Pages Count
10
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Publisher
Elsevier
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DOI
10.1016/j.bmc.2007.02.034