60027-35-2Relevant academic research and scientific papers
New 4-aryl-1,3,2-oxathiazolylium-5-olates: Chemical synthesis and photochemical stability of a novel series of S-nitrosothiols
Eilertsen, Monica,Allin, Steve M.,Pearson, Russell J.
, p. 1106 - 1110 (2018/02/28)
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.
AMIDO-ISOTHIAZOLE COMPOUNDS AND THEIR USE AS INHIBITORS OF 11BETA-HSD1 FOR THE TREATMENT OF METABOLIC SYNDROME AND RELATED DISORDERS
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Page/Page column 77-78, (2010/12/31)
The present invention pertains generally to the field of therapeutic compounds. More specifically the present invention pertains to certain amido-isothiazole compounds that, inter alia, inhibit 11β-hydroxysteroid dehydrogenase type 1 (11β-HSD1). The present invention also pertains to pharmaceutical compositions comprising such compounds, and the use of such compounds and compositions, both in vitro and in vivo, to inhibit 11β-hydroxysteroid dehydrogenase type 1; to treat disorders that are ameliorated by the inhibition of 11β-hydroxysteroid dehydrogenase type 1; to treat the metabolic syndrome, which includes disorders such as type 2 diabetes and obesity, and associated disorders including insulin resistance, hypertension, lipid disorders and cardiovascular disorders such as ischaemic (coronary) heart disease; to treat CNS disorders such as mild cognitive impairment and early dementia, including Alzheimer's disease; etc.
4-Aryl-1,3,2-oxathiazolylium-5-olates as pH-controlled NO-donors: The next generation of S-nitrosothiols
Lu, Dongning,Nadas, Janos,Zhang, Guisheng,Johnson, Wesley,Zweier, Jay L.,Cardounel, Arturo J.,Villamena, Frederick A.,Wang, Peng George
, p. 5503 - 5514 (2008/02/07)
S-Nitrosothiols (RSNOs) are important exogenous and endogenous sources of nitric oxide (NO) in biological systems. A series of 4-aryl-1,3,2- oxathiazolylium-5-olates derivatives with varying aryl para-substituents (-CF3, -H, -Cl, and -OCH3) were synthesized. These compounds were found to release NO under acidic condition (pH = 5). The decomposition pathway of the aryloxathiazolyliumolates proceeded via an acid-catalyzed ring-opening mechanism after which NO was released and an S-centered radical was generated. Electron paramagnetic resonance (EPR) spin trapping studies were performed to detect NO and the S-centered radical using the spin traps of iron(II) N-methyl-D-glucamine dithiocarbamate [(MGD) 2-FeII] and 5,5-dimethyl-1-pyrroline N-oxide (DMPO). Also, EPR spin trapping and UV-vis spectrophotometry were used to analyze the effect of aryl para substitution on the NO-releasing property of aryloxathiazolyliumolates. The results showed that the presence of an electron-withdrawing substituent such as -CF3 enhanced the NO-releasing capability of the aryloxathiazolyliumolates, whereas an electron-donating substituent like methoxy (-OCH3) diminished it. Computational studies using density functional theory (DFT) at the PCM/B3LYP/6-31+G*7/B3LYP/6-31G* level were used to rationalize the experimental observations. The aryloxathiazolyliumolates diminished susceptibility to reduction by ascorbate or gluthathione, and their capacity to cause vasodilation as compared to other S-nitrosothiols suggests potential application in biological systems.
Viscosity-dependent Fluorescence and Low-temperature Photochemistry of Mesionic 4-Phenyl-1,3,2-oxathiazolylium-5-olate
Harrit, Niels,Holm, Arne,Dunkin, Ian R.,Poliakoff, Martin,Turner, James J.
, p. 1227 - 1238 (2007/10/02)
Irradiation of 4-phenyl-1,3,2-oxathiazolylium-5-olate (1) at cryogenic temperatures leads to formation of benzonitrile sulphide (4) and phenyl(nitrosothio)ketene (6) as primary products.They have been characterized by u.v. and i.r. spectroscopy.The relative yields of (4) and (6) depend strongly on the local viscosity of the medium.For example, poly(vinyl chloride) favours the formation of (4), whereas solid nitrogen favours (6).The observation of a strong fluorescence is also conditioned by a rigid environment.A vibrational fine structure extending half way through the main absorption band of (1) indicates the existence of a dissociative pathway in the excited singlet-state potential energy surface.This pathway is identified with the formation of (6).Isotopic labelling has been used to characterize (6) and the i.r. absorptions of its cis-trans-isomers have been located.The cis-isomer of (6) can regenerate (1) upon irradiation; similar treatment of the trans-isomer leads to the resonance-stabilized radical phenyl(oxomethylene)thiyl (7).
