236413-32-4Relevant articles and documents
The synthesis and structure of the derivatives of 2-deoxy-2-hydroxyimino-D-lyxo-hexopyranosyl-L-cysteine and -thiophenol
Liberek, Beata,Konitz, Antoni,Frankowski, Ryszard,Smiatacz, Zygfryd
, p. 151 - 158 (2000)
3,4,6-Tri-O-acetyl-2-deoxy-2-hydroxyimino-β and -α-D-lyxo-hexopyranosides of thiophenol (3, 4) and the methyl ester of N-benzoyl-L-cysteine have been synthesised by condensation of 3,4,6-tri-O-acetyl-2-deoxy-2-nitroso-α-D-galactopyranosyl chloride with thiophenol and the L-cysteine derivative, respectively. The conformation of the sugar residue and configuration of the anomeric centre as well as of the hydroxyimino group were established on the basis of the 1H NMR (DQF-COSY, ROESY, TOCSY) spectrometric techniques and polarimetric data. Additionally, the structure of S-[3,4,6-tri-O-acetyl-2-deoxy-2-(Z)-hydroxyimino-β-D-lyxo-hexopyranosyl]-thiophenol (3) was supported by X-ray diffraction data. Copyright (C) 2000 Elsevier Science Ltd.
Controllable hydrogen sulfide donors and their activity against myocardial ischemia-reperfusion injury
Zhao, Yu,Bhushan, Shashi,Yang, Chuntao,Otsuka, Hiroyuki,Stein, Jason D.,Pacheco, Armando,Peng, Bo,Devarie-Baez, Nelmi O.,Aguilar, Hector C.,Lefer, David J.,Xian, Ming
, p. 1283 - 1290 (2013/07/26)
Hydrogen sulfide (H2S), known as an important cellular signaling molecule, plays critical roles in many physiological and/or pathological processes. Modulation of H2S levels could have tremendous therapeutic value. However, the study on H2S has been hindered due to the lack of controllable H2S releasing agents that could mimic the slow and moderate H2S release in vivo. In this work we report the design, synthesis, and biological evaluation of a new class of controllable H 2S donors. Twenty-five donors were prepared and tested. Their structures were based on a perthiol template, which was suggested to be involved in H2S biosynthesis. H2S release mechanism from these donors was studied and proved to be thiol-dependent. We also developed a series of cell-based assays to access their H2S-related activities. H9c2 cardiac myocytes were used in these experiments. We tested lead donors' cytotoxicity and confirmed their H2S production in cells. Finally we demonstrated that selected donors showed potent protective effects in an in vivo murine model of myocardial ischemia-reperfusion injury, through a H 2S-related mechanism.
The use of phosphonium anhydrides for the synthesis of 2-oxazolines, 2-thiazolines and 2-dihydrooxazine under mild conditions
Petersson, Maria J.,Jenkins, Ian D.,Loughlin, Wendy A.
supporting information; experimental part, p. 739 - 746 (2009/06/20)
β-Hydroxy amides 6 and 7 were treated with triphenylphosphonium anhydride trifluoromethane sulfonate (3), or the cyclic analogue 4, to generate 2-oxazolines 5 and 8 under mild conditions. The reaction was optimised by examining the number of equivalents of reagents 3 or 4, or diisopropylethyl amine required to best effect cyclisation. The effects of altering the reaction temperature, reaction time, concentration, solvent, and addition rate also were investigated. However, it was found that use of a trityl group to block reaction at the hydroxyl or thiol group of the starting amides, and subsequent in situ detritylation, in the absence of base, led to greatly improved yields. Reagent 4 offered significant advantages in the purification of products and was used to dehydrate a range of trityl derivatives to form simple oxazolines, thiazolines, and a dihydro-1,3-oxazine, in high yield (85-99%), as well as a tetrahydro-1,3-oxazepine (31%).
Methyl esters of N-protected-O-or -S-(4,6-di-O-acetyl-2,3-dideoxy-D-erythro-hex-2 - enopyranosyl)-L-serine, -L-threonine and -L-cysteine: Synthesis and some transformations
Liberek,Smiatacz
, p. 989 - 996 (2007/10/03)
Methyl esters of N-tosyl-O-(4,6-di-O-acetyl-2,3-dideoxy-D-erythro-hex-2-enopyranosyl)-L-serine (5), -L-threonine (6) and N-benzoyl-5-(4,6-di-O-acetyl-2,3-dideoxy-α-D-erythro-hex-2-enopyranosyl)-L -cysteine (7) have been synthesized by condensation of 3,4,6-tri-O-acetyl-1,5-anhydro-2-deoxy-D-arabino-hex-1-enitol (1) with respective derivatives of L-serine (2), L-threonine (3) and L-cysteine (4), cis-Hydroxylation and epoxydation of 2,3-unsaturated glycopyranoside 5 afforded O-glycosyl-L-serine derivatives with α-D-manno (8, 9), 2,3-anhydro-α-D-manno (10) and 2,3-anhydro-α-D-allo (11) structures, respectively. The structure of compounds as well as conformation of the sugar residue and configuration at the anomeric centre were established on the basis of the 1H and 13C NMR (DQF-COSY, TOCSY, HMBC), IR, MS (FD) spectrometric techniques and polarimetric data.
Synthesis and properties of derivatives of 2-deoxy-2-hydroxyimino-D-arabino-hexopyranosyl-L-cysteine and -thiophenol
Liberek,Frankowski,Smiatacz
, p. 1153 - 1161 (2007/10/03)
3,4,6-Tri-O-acetyl-2-deoxy-2-hydroxyimino-α- and -β-D-arabino-hexopyranosides of thiophenol (3-5) as well as the methyl ester of N-benzoyl-L-cysteine (6,7) have been synthesized by condensation of 3,4,6-tri-O-acetyl-2-deoxy-2-nitroso-α-D-glucopyranosyl chloride (1) with thiophenol and the L-cysteine derivative, respectively. The glycopyranosides of thiophenol were modified at C-2 and C-3 positions to afford thiophenol derivatives with 2-deoxy-2-hydroxyamino-α-D-glucopyranosyl (13,14), 3-azido-2,3-dideoxy-2-hydroxyimmo-α-D-arabino-(8), β-D-arabino-(10), and α-D-ribo-hexopyranosyl (9) structures. The conformation of the sugar residue and configuration at the anomeric center and of the hydroxyimino group were established on the basis of the 1H, 13C, 15N NMR (DQF-COSY, TOCSY, NOESY, ROESY, HSQC, HMBC and HMBCN) spectrometric techniques and polarimetric data.
