New 4-aryl-1,3,2-oxathiazolylium-5-olates: Chemical synthesis and photochemical stability of a novel series of S-nitrosothiols |
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Authors: | Monica Eilertsen Steve M Allin Russell J Pearson |
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Institution: | 1. School of Pharmacy, Keele University, Hornbeam Building, Keele, Staffordshire ST5 5BG, UK;2. Department of Chemistry and Forensics, School of Science and Technology, Nottingham Trent University, Nottingham NG11 8NS, UK |
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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 moiety 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 21 and 37%. 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. |
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Keywords: | NO-donating Nitric oxide Oxathiazolylium-5-olates Photochemical stability |
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