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Design and synthesis of substituted imidazole and triazole N-phenylbenzo[d]oxazolamine inhibitors of retinoic acid metabolizing enzyme CYP26

Pautus, S., Aboraia, A. S., Bassett, C. E., Brancale, Andrea, Coogan, Michael Peter and Simons, Clare 2009. Design and synthesis of substituted imidazole and triazole N-phenylbenzo[d]oxazolamine inhibitors of retinoic acid metabolizing enzyme CYP26. Journal of Enzyme Inhibition and Medicinal Chemistry 24 (2) , pp. 487-498. 10.1080/14756360802218334

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Abstract

The design of N-phenylbenzo[d]oxazolamines as CYP26A1 inhibitors involved ligand docking experiments using molecular modeling (FlexX) and analysis of ligand interactions at the binding domain. The synthesis of the benzooxazol-2-yl-[phenyl-imidazol-1-yl-methyl)phenyl]amines was achieved by cyclisation of the corresponding isothiocyanates with subsequent introduction of the haem-binding heterocycle. Triazole and tetrazole derivatives were also prepared for comparison with the lead imidazole derivative. The benzooxazol-2-yl-[phenyl-imidazol-1-yl-methyl)phenyl]amines with small substituents in the phenyl ring were moderately potent CYP26A1 inhibitors (IC50 8 and 12 μM) and comparable with liarozole (IC50 7 μM).

Item Type: Article
Date Type: Publication
Status: Published
Schools: Chemistry
Pharmacy
Subjects: R Medicine > RS Pharmacy and materia medica
Uncontrolled Keywords: N-phenylbenzo[d]oxazolamines, molecular modeling, retinoic acid, CYP26A1, enzyme inhibition, IC50
Publisher: Informa Healthcare
ISSN: 1475-6366
Last Modified: 02 Jan 2018 21:26
URI: http://orca.cf.ac.uk/id/eprint/6100

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