New 4-aryl-1,3,2-oxathiazolylium-5-olates: chemical synthesis and photochemical stability of a novel series of S-nitrosothiols

Abstract

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.

Citation

(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, 1106-1110. https://doi.org/10.1016/j.bmcl.2018.01.059

• Acceptance Date: Jan 27, 2018
• Publication Date: Apr 1, 2018
• Journal: Bioorganic and Medicinal Chemistry Letters
• Print ISSN: 0960-894X
• Publisher: Elsevier
• Pages: 1106-1110
• DOI: https://doi.org/10.1016/j.bmcl.2018.01.059
• Keywords: S-Nitrosothiols; NO-donating; Nitric oxide; Oxathiazolylium-5-olates; Photochemical stability
• Publisher URL: https://www.sciencedirect.com/science/article/pii/S0960894X18300702