Heme oxygenase inhibition by 2-oxy-substituted 1-(1H-imidazol-1-yl)-4-phenylbutanes: Effect of halogen substitution in the phenyl ring

Roman, Gheorghe, Riley, John, Vlahakis, Jason, Kinobe, Robert, Brien, James, Nakatsu, Kanji, and Szarek, Walter (2007) Heme oxygenase inhibition by 2-oxy-substituted 1-(1H-imidazol-1-yl)-4-phenylbutanes: Effect of halogen substitution in the phenyl ring. Bioorganic & Medicinal Chemistry, 15. pp. 3225-3234.

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Abstract

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.

Item ID: 80734
Item Type: Article (Research - C1)
ISSN: 1464-3391
Copyright Information: © 2007 Elsevier Ltd. All rights reserved.
Funders: Canadian Institutes of Health Research
Projects and Grants: MOP 64305
Date Deposited: 21 Mar 2024 01:21
FoR Codes: 34 CHEMICAL SCIENCES > 3405 Organic chemistry > 340503 Organic chemical synthesis @ 50%
32 BIOMEDICAL AND CLINICAL SCIENCES > 3214 Pharmacology and pharmaceutical sciences > 321401 Basic pharmacology @ 50%
SEO Codes: 28 EXPANDING KNOWLEDGE > 2801 Expanding knowledge > 280102 Expanding knowledge in the biological sciences @ 50%
28 EXPANDING KNOWLEDGE > 2801 Expanding knowledge > 280105 Expanding knowledge in the chemical sciences @ 50%
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