Iodoetherification as a strategy towards sp 3-rich scaffolds for drug discovery

Barnes, Lydia; Birkinshaw, Timothy N; Senior, Aaron J; Siles Brügge, Oscar; Lewis, William; Argent, Stephen P; Moody, Christopher J; Nortcliffe, Andrew

Abstract

Functionalised tetrahydropyran and spirooxepane scaffolds were prepared utilising an iodoetherification strategy and elaborated to demonstrate their potential use in library synthesis. The iodoetherification products could be readily transformed to the corresponding azides that could be further functionalised via copper-catalysed azide-alkyne cycloaddition or reduction to the amine. The lead-likeness and three-dimensionality of the scaffolds were examined and compared to commercial libraries.

Citation

Barnes, L., Birkinshaw, T. N., Senior, A. J., Siles Brügge, O., Lewis, W., Argent, S. P., …Nortcliffe, A. (2024). Iodoetherification as a strategy towards sp 3-rich scaffolds for drug discovery. Bioorganic and Medicinal Chemistry, 101, Article 117636. https://doi.org/10.1016/j.bmc.2024.117636

• Journal Article Type: Article
• Acceptance Date: Feb 7, 2024
• Online Publication Date: Feb 10, 2024
• Publication Date: Mar 1, 2024
• Deposit Date: Feb 7, 2024
• Publicly Available Date: Feb 11, 2025
• Journal: Bioorganic and Medicinal Chemistry
• Print ISSN: 0968-0896
• Electronic ISSN: 1464-3391
• Publisher: Elsevier
• Peer Reviewed: Peer Reviewed
• Volume: 101
• Article Number: 117636
• DOI: https://doi.org/10.1016/j.bmc.2024.117636
• Keywords: Organic Chemistry; Clinical Biochemistry; Drug Discovery; Pharmaceutical Science; Molecular Biology; Molecular Medicine; Biochemistry
• Public URL: https://nottingham-repository.worktribe.com/output/31151642
• Publisher URL: https://www.sciencedirect.com/science/article/abs/pii/S0968089624000506