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Synthesis of highly substituted 1,2-diazetidin-3-ones, small ring scaffolds for drug discovery

Santos, Marilia S.; Nortcliffe, Andrew; Lewis, William; Bradshaw, Tracey D; Moody, Christopher J.

Authors

Marilia S. Santos

Andrew Nortcliffe

William Lewis

Tracey D Bradshaw

Christopher J. Moody



Abstract

1,2-Diazetidin-3-ones are readily accessible, small ring scaffolds that upon functionalization have the potential to produce diverse 3-dimensional structures for drug discovery. Thus treatment of diazo hydrazides, obtained from simple hydrazides and malonyl half ester derivatives, followed by diazo transfer, with catalytic amounts of rhodium (II) acetate dimer results in intramolecular carbenoid N–H insertion to give 1,2-diazetidin-3-ones. Although subsequent functionalization reactions could be hampered by the lability of the 4-membered ring, a wide range of new derivatives was available by deprotection at N-1, and subsequent amide or urea formation. The structures of four four-membered rings was confirmed by X-ray crystallography; the compounds showed modest growth inhibitory activity in mammary carcinoma cells.

Journal Article Type Article
Journal Chemistry - a European Journal
Print ISSN 0947-6539
Electronic ISSN 1521-3765
Publisher Wiley
Peer Reviewed Peer Reviewed
APA6 Citation Santos, M. S., Nortcliffe, A., Lewis, W., Bradshaw, T. D., & Moody, C. J. (in press). Synthesis of highly substituted 1,2-diazetidin-3-ones, small ring scaffolds for drug discovery. Chemistry - A European Journal, doi:10.1002/chem.201801309
DOI https://doi.org/10.1002/chem.201801309
Publisher URL https://onlinelibrary.wiley.com/doi/abs/10.1002/chem.201801309
Copyright Statement Copyright information regarding this work can be found at the following address: http://eprints.nottingh.../end_user_agreement.pdf
Additional Information This is the peer reviewed version of the following article: Santos, Marilla S and Nortcliffe, Andrew and Lewis, William and Bradshaw, Tracey D and Moody, Christopher J (2018) Synthesis of highly substituted 1,2-diazetidin-3-ones, small ring scaffolds for drug discovery. Chemistry - a European Journal, doi:10.1002/chem.201801309, which has been published in final form at https://onlinelibrary.w...10.1002/chem.201801309. This article may be used for non-commercial purposes in accordance with Wiley Terms and Conditions for Self-Archiving.

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Copyright Statement
Copyright information regarding this work can be found at the following address: http://eprints.nottingham.ac.uk/end_user_agreement.pdf





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