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 ORCID: https://orcid.org/0000-0002-9728-3419, Coogan, Michael Peter and Simons, Clare ORCID: https://orcid.org/0000-0002-9487-1100 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:	05 Jan 2024 05:54
URI:	https://orca.cardiff.ac.uk/id/eprint/6100

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