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New Routes to Aryl Cyclic Sulfoximines for Medicinal Chemistry


Department of Chemistry

About the Project

Background
The sulfoximine functional group is becoming increasingly popular within medicinal chemistry groups – notably, sulfoximines have featured in potential cancer treatments in clinical trials such as AZD6738 developed by AstraZeneca.[1,2] Consequently, there is great interest in developing new synthetic methodology to access structurally diverse sulfoximines. However, there are very limited examples that allow cyclic sulfoximines to be functionalised. In order to explore new areas of 3-D pharmaceutical space, we will explore general methodology for the stereoseective arylation of cyclic sulfoximines. This will deliver novel 3-D sulfoximines for use in medicinal chemistry, via the O’Brien group’s links with the pharmaceutical industry (AstraZeneca, Pfizer, Asahi Kasei).

Objectives
1. Arylation of 5-ring cyclic sulfoximines at the 2- and 3-positions
2. Arylation of 6-ring cyclic sulfoximines at the 2-, 3- and 4-positions
3. Explore applications of 3-D cyclic aryl sulfoximines in medicinal chemistry

Experimental Approach
There are three stages to this project, all of which require different types of synthetic methodology development. First, methods will need to be developed to enable the large-scale synthesis of a range of cyclic sulfoximine vinyl bromides/iodides and enol triflates (with different nitrogen protecting groups). Then, their use in a range of medicinally-relevant Suzuki-Miyaura cross-coupling reactions using aryl boronic acids will be studied. Finally, stereoselective hydrogenation will give the stereodefined aryl sulfoximines[3,4] which will be deprotected and be available for use in medicinal chemistry programmes.

Novelty
There are very few examples of the functionalisation of cyclic sulfoximines and cyclic aryl sulfoximines are an unstudied class of compound.

Training
This project will provide state-of-the-art training in modern synthetic methodology and medicinal chemistry. The graduating PhD student will be fully equipped for a future career in the pharmaceutical industry. All Chemistry research students have access to our innovative Doctoral Training in Chemistry (iDTC): cohort-based training to support the development of scientific, transferable and employability skills: https://www.york.ac.uk/chemistry/postgraduate/idtc/

The Department of Chemistry holds an Athena SWAN Gold Award and is committed to supporting equality and diversity for all staff and students. The Department strives to provide a working environment which allows all staff and students to contribute fully, to flourish, and to excel: https://www.york.ac.uk/chemistry/ed/.

You should hold or expect to achieve the equivalent of at least a UK upper second class degree in Chemistry or a related subject. Please check the entry requirements for your country: https://www.york.ac.uk/study/international/your-country/

For more information about the project, click on the supervisor’s name above to email the supervisor. For more information about the application process or funding, please click on email institution

Funding Notes

This project is available to students from any country who can fund their own studies.

The Department of Chemistry at the University of York is pleased to offer Wild Fund Scholarships. Applications are welcomed from those who meet the PhD entry criteria from any country outside the UK. Scholarships will be awarded on supervisor support, academic merit, country of origin, expressed financial need and departmental strategy. For further details and deadlines, please see our website: View Website

References

1 https://dx.doi.org/10.1021/acs.jmedchem.0c00960
2 Lücking, U. Angew. Chem. Int. Ed. 2013, 52, 9399.
3 Fang, Y. et al. Tetrahedron Lett. 2016, 57, 1460.
4 Campbell, P. S.; Jamieson, C.; Simpson, I.; Watson, A. J. B. Chem. Commun. 2018, 54, 46.

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