Expedient synthesis of an atypical oxazolidinone compound library

Cully, Sarah J.; Storr, Thomas E.; Rawling, Michael J.; Abeysena, Induka R.; Hamza, Daniel; Jones, Geraint; Pearce, Christopher A.; Quddus, Abdul; Lewis, William; Stockman, Robert A.

Abstract

In order to address the current downturn in the drug discovery pipeline, initiatives are being undertaken to synthesise screening libraries of sp3-rich, low molecular weight compounds. As part of the European Lead Factory initiative, the synthesis and derivatisation of a simple hexahydrooxazolo[5,4-c]pyridin-2(1H)-one bicyclic carbamate has been achieved. The synthetic route employed involved a telescoped hetero-Diels-Alder/[2,3]-sigmatropic rearrangement/cyclisation sequence to deliver the desired core scaffold containing two points for further diversification. When applied, this synthesis was found to be robust and scalable which allowed the production of a 155 compound library.

Citation

Cully, S. J., Storr, T. E., Rawling, M. J., Abeysena, I. R., Hamza, D., Jones, G., Pearce, C. A., Quddus, A., Lewis, W., & Stockman, R. A. (2016). Expedient synthesis of an atypical oxazolidinone compound library. Bioorganic and Medicinal Chemistry, 24(21), 5249-5257. https://doi.org/10.1016/j.bmc.2016.08.046

• Journal Article Type: Article
• Acceptance Date: Aug 25, 2016
• Online Publication Date: Aug 27, 2016
• Publication Date: Nov 1, 2016
• Deposit Date: Sep 1, 2016
• Publicly Available Date: Sep 1, 2016
• Journal: Bioorganic and Medicinal Chemistry
• Print ISSN: 0968-0896
• Electronic ISSN: 1464-3391
• Publisher: Elsevier
• Peer Reviewed: Peer Reviewed
• Volume: 24
• Issue: 21
• Pages: 5249-5257
• DOI: https://doi.org/10.1016/j.bmc.2016.08.046
• Public URL: https://nottingham-repository.worktribe.com/output/804261
• Publisher URL: http://www.sciencedirect.com/science/article/pii/S096808961630654X
• Contract Date: Sep 1, 2016