Home > Research > Publications & Outputs > Design and synthesis of substituted imidazole a...
View graph of relations

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

Research output: Contribution to Journal/MagazineJournal articlepeer-review

Published

Standard

Design and synthesis of substituted imidazole and triazole N-phenylbenzo[d]oxazolamine inhibitors of retinoic acid metabolizing enzyme CYP26. / Pautus, Stephane ; Aboraia, Ahmed S.; Bassett, Claire E. et al.
In: Journal of Enzyme Inhibition and Medicinal Chemistry, Vol. 24, No. 2, 2009, p. 487-498.

Research output: Contribution to Journal/MagazineJournal articlepeer-review

Harvard

Pautus, S, Aboraia, AS, Bassett, CE, Brancale, A, Coogan, M & Simons, C 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, vol. 24, no. 2, pp. 487-498. https://doi.org/10.1080/14756360802218334

APA

Pautus, S., Aboraia, A. S., Bassett, C. E., Brancale, A., Coogan, M., & Simons, C. (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), 487-498. https://doi.org/10.1080/14756360802218334

Vancouver

Pautus S, Aboraia AS, Bassett CE, Brancale A, Coogan M, Simons C. 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. 2009;24(2):487-498. doi: 10.1080/14756360802218334

Author

Pautus, Stephane ; Aboraia, Ahmed S. ; Bassett, Claire E. et al. / Design and synthesis of substituted imidazole and triazole N-phenylbenzo[d]oxazolamine inhibitors of retinoic acid metabolizing enzyme CYP26. In: Journal of Enzyme Inhibition and Medicinal Chemistry. 2009 ; Vol. 24, No. 2. pp. 487-498.

Bibtex

@article{7f826f5f7d254c0487f5194802cacb8b,
title = "Design and synthesis of substituted imidazole and triazole N-phenylbenzo[d]oxazolamine inhibitors of retinoic acid metabolizing enzyme CYP26",
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). ",
author = "Stephane Pautus and Aboraia, {Ahmed S.} and Bassett, {Claire E.} and Andrea Brancale and Michael Coogan and Claire Simons",
year = "2009",
doi = "10.1080/14756360802218334",
language = "English",
volume = "24",
pages = "487--498",
journal = "Journal of Enzyme Inhibition and Medicinal Chemistry",
issn = "1475-6374",
publisher = "Informa Healthcare",
number = "2",

}

RIS

TY - JOUR

T1 - Design and synthesis of substituted imidazole and triazole N-phenylbenzo[d]oxazolamine inhibitors of retinoic acid metabolizing enzyme CYP26

AU - Pautus, Stephane

AU - Aboraia, Ahmed S.

AU - Bassett, Claire E.

AU - Brancale, Andrea

AU - Coogan, Michael

AU - Simons, Claire

PY - 2009

Y1 - 2009

N2 - 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).

AB - 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).

U2 - 10.1080/14756360802218334

DO - 10.1080/14756360802218334

M3 - Journal article

VL - 24

SP - 487

EP - 498

JO - Journal of Enzyme Inhibition and Medicinal Chemistry

JF - Journal of Enzyme Inhibition and Medicinal Chemistry

SN - 1475-6374

IS - 2

ER -