Eilertsen, M, Allin, SM and Pearson, RJ (2018) New 4-aryl-1,3,2-oxathiazolylium-5-olates: chemical synthesis and photochemical stability of a novel series of S-nitrosothiols. Bioorganic and Medicinal Chemistry Letters, 28 (6). pp. 1106-1110. ISSN 1464-3405

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Abstract S-Nitrosothiols (RSNOs) remain one of the most popular classes of NO-donating compounds due to their ability to release nitric oxide (NO) under non-enzymatic means whilst producing an inert disulphide by-product. However, alligning these compounds to the different biological fields of NO research has proved to be problematic due to the inherent instability of such compounds under a variety of conditions including heat, light and the presence of copper ions. 1,3,2-Oxathiazolylium-5-olates (OZOs) represent an interesting subclass of S-nitrosothiols that lock the –SNO moeity into a five membered heterocyclic ring in an attempt to improve the compound’s overall stability. The synthesis of a novel series of halogen-containing OZOs was comprehensively studied resulting in a seven-step route and overall yields ranging between 4% and 28%. The photochemical stability of these compounds was assessed to determine if S-nitrosothiols locked within these mesoionic ring systems can offer greater stability and thereby release NO in a more controllable fashion than their non-cyclic counterparts.

Item Type: Article
Uncontrolled Keywords: S-Nitrosothiols; NO-donating; Nitric oxide; Oxathiazolylium-5-olates; Photochemical stability
Subjects: R Medicine > R Medicine (General)
R Medicine > RM Therapeutics. Pharmacology
Divisions: Faculty of Medicine and Health Sciences > School of Pharmacy
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Depositing User: Symplectic
Date Deposited: 13 Feb 2018 10:28
Last Modified: 31 Jan 2019 01:30
URI: https://eprints.keele.ac.uk/id/eprint/4453

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