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New Routes to Cyclic Sulfoximine 3-D Fragments for Medicinal Chemistry

  • Full or part time
  • Application Deadline
    Applications accepted all year round
  • Self-Funded PhD Students Only
    Self-Funded PhD Students Only

Project Description

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. 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 the functionalisation of cyclic sulfoximines. This will deliver novel 3-D fragments for use in medicinal chemistry, via the O’Brien group’s links with the pharmaceutical industry.

Objectives
1. Explore the lithiation-trapping of cyclic sulfoximines
2. Explore the arylation of cyclic sulfoximines at different positions
3. Design and synthesise 3-D fragments containing sulfoximines

Experimental Approach
A wide range of different cyclic sulfoximines will be synthesised form the corresponding sulfides by oxidation and N-protection using standard methods.1 Then, conditions for the lithiation-trapping of the cyclic sulfoximines will be optimised. In particular, focus will be on the development of diastereoselective reactions and factors affecting the diastereoselectivity will be explored. Next, the arylation will be studied using relevant literature procedures.2-4 In particular, we plan that by suitable variation of the substituent on the nitrogen conditions for the separate diastereoselective synthesis of trans- and cis-diastereoisomers will be optimised. To fully explore the scope and limitations of this novel methodology, different ring sizes and a wide range of aryl halides, including medicinally relevant electron deficient heteroaromatics, will be utilised. The use of chiral bases and/or chiral phosphine ligands should provide a route to enantioenriched products. With methodology established, we will prepare a family of designed 3-D fragments.

Novelty
There are very few examples of the functionalisation of cyclic sulfoximines.

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 expect 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/

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 Zenzola, M. et al. Angew. Chem. Int. Ed. 2016, 55, 7203.
2 Zhou, G. et al. Tetrahedron Lett. 2010, 51, 939.
3 René, O. et al. Org. Lett. 2014, 16, 3468.
4 Sirvent, J. A. et al. Synthesis, 2017, 49, 1024.

How good is research at University of York in Chemistry?

FTE Category A staff submitted: 47.06

Research output data provided by the Research Excellence Framework (REF)

Click here to see the results for all UK universities

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