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Synthesis and CYP26A1 inhibitory activity of 1-[benzofuran-2-yl-(4-alkyl/aryl-phenyl)-methyl]-1H-triazoles

Pautus, Stephane Mathieu, Yee, Sook Wah, Jayne, Martyn John, Coogan, Michael Peter and Simons, Claire 2006. Synthesis and CYP26A1 inhibitory activity of 1-[benzofuran-2-yl-(4-alkyl/aryl-phenyl)-methyl]-1H-triazoles. Bioorganic & Medicinal Chemistry 14 (11) , pp. 3643-3653. 10.1016/j.bmc.2006.01.018

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Abstract

Methodology previously described by our group was applied to the preparation of a series of 4-alkyl/aryl-substituted 1-[benzofuran-2-yl-phenylmethyl]-1H-triazoles. The [1,2,4]-triazole derivatives were prepared for a range of alkyl and aryl substituents, and for the 4-methyl, 4-ethyl, 4-ipropyl, 4-tbutyl, 4-phenyl and 4-chlorophenyl derivatives, the minor [1,3,4]-triazole isomer also isolated. All the triazole derivatives were evaluated for CYP26A1 inhibitory activity using a MCF-7 cell-based assay. The 4-ethyl and 4-phenyl-1,2,4-triazole derivatives displayed inhibitory activity (IC50 4.5 and 7 μM, respectively) comparable with that of the CYP26 inhibitor liarozole (IC50 7 μM). Using a CYP26A1 homology model (based on CYP3A4) template, docking experiments were performed with MOE with multiple hydrophobic interactions observed in addition to coordination between the triazole nitrogen and the haem transition metal.

Item Type: Article
Date Type: Publication
Status: Published
Schools: Chemistry
Pharmacy
Subjects: R Medicine > RS Pharmacy and materia medica
Uncontrolled Keywords: 1-[Benzofuran-2-yl-(4-alkyl/aryl-phenyl)-methyl]-1H-triazoles; CYP26A1; Enzyme inhibition; MCF-7; Molecular modelling
Publisher: Elsevier
ISSN: 0968-0896
Last Modified: 10 Oct 2017 13:27
URI: http://orca-mwe.cf.ac.uk/id/eprint/13999

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