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

Eilertsen, M., Allin, S.M. ORCID: 0000-0001-5198-9339 and Pearson, R.J., 2018. New 4-aryl-1,3,2-oxathiazolylium-5-olates: chemical synthesis and photochemical stability of a novel series of S-nitrosothiols. Bioorganic & Medicinal Chemistry Letters, 28 (6), pp. 1106-1110. ISSN 0960-894X

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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 byproduct. 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 Snitrosothiols 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: Journal article
Publication Title: Bioorganic & Medicinal Chemistry Letters
Creators: Eilertsen, M., Allin, S.M. and Pearson, R.J.
Publisher: Elsevier
Date: 1 April 2018
Volume: 28
Number: 6
ISSN: 0960-894X
Identifiers:
NumberType
10.1016/j.bmcl.2018.01.059DOI
S0960894X18300702Publisher Item Identifier
Rights: © 2018 The Author(s). Published by Elsevier Ltd. This is an open access article under the CC BY-NC-ND license (http://creativecommons.org/licenses/by-nc-nd/4.0/).
Divisions: Schools > School of Science and Technology
Depositing User: Jonathan Gallacher
Date Added: 16 Mar 2018 15:51
Last Modified: 13 Apr 2018 13:27
URI: http://irep.ntu.ac.uk/id/eprint/33013

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