13165-79-2Relevant academic research and scientific papers
Piloty's acid derivative with improved nitroxyl-releasing characteristics
Aizawa, Kazuyuki,Nakagawa, Hidehiko,Matsuo, Kazuya,Kawai, Kodai,Ieda, Naoya,Suzuki, Takayoshi,Miyata, Naoki
supporting information, p. 2340 - 2343 (2013/05/09)
Recent studies have shown that nitroxyl (HNO) (1HNO/ 3NO-), which is the one-electron-reduced form of nitric oxide (NO), has unique biological activities, especially in the cardiovascular system, and HNO-releasing agents may have therapeutic potential. Since few HNO donors are available for use under physiological conditions, we synthesized and evaluated a series of Piloty's acid (PA) derivatives and evaluated their HNO-releasing activity under physiological conditions. N-Hydroxy-2- nitrobenzenesulfonamide (17) was the most efficient HNO donor among our synthesized PA derivatives, including the lead compound, 2-bromo-N- hydroxybenzenesulfonamide (2). The high HNO-releasing activity is suggested to be due to electronic and steric effects. Compound 17 may be a useful tool for biological experiments.
Imidazoline derivatives as alpha-1A adrenoceptor ligands
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Page/Page column 13, (2010/02/11)
Compound of formula (I) or a pharmaceutically acceptable salt or solvate thereof are disclosed. Such compounds are useful in the treatment of Alpha-1A mediated diseases or conditions such as urinary incontinence.
Flow cell electrosynthesis of phenylhydroxylamines. In situ reaction with arenesulfonyl chlorides. A convenient route to arenesulfinic acids synthesis.
Moinet, C.,Raoult, E.
, p. 214 - 221 (2007/10/02)
First, electrosyntheses of phenylhydroxylamines in a flow cell fitted with porous cathode and two counter-electrodes are described.Good yields are attained when electrolyses are performed in buffered aqueous organic or aqueous media.Reaction between p-toluenesulfonyl chloride and N-(3-chloro-4-methylphenyl)hydroxylamine, at the outlet of the cell, leads to a N-sulfonylated phenylhydroxylamine (N-addition); hydrolysis of this latter occurs in aqueous basic media to give the corresponding nitrosobenzene and sodium p-toluenesulfinate.As a result, some arenesulfinic acids have been directly obtained after reaction of arenesulfonyl chloride with sodium salt of 3-hydroxylaminobenzoate and 3-hydroxylaminobenzenesulfonate in aqueous phosphate buffer (pH 7).Next, an examination of the reaction of p-toluenesulfonyl chloride with phenylhydroxylamine in organic solvent, in the presence of triethylamine or of sodium carbonate, shows the importance of experimental conditions to control N-addition or O-addition.Addition of some arenesulfonyl chlorides to phenylhydroxylamine, in ether or dichloromethane containing sodium carbonate, gives only the N-sulfonylated phenylhydroxylamines.These compounds lead to nitrosobenzene and arenesulfinate anions in aqueous basic media.Aliphatic or aromatic sulfinic acids can be prepared in this way.
Sulfinic Acids and Related Compounds 23. Preparation of Sulfinic Acids by the Reaction of Sulfonyl Halides with Thiols
Lee, Chew,Field, Lamar
, p. 391 - 397 (2007/10/02)
The reaction of arene- and alkanesulfonyl halides with p-thiocresol in the presence of triethylamine at -76 deg C gives triethylammonium sulfinates, which after acidification afford sulfinic acids of 95 - 100 percent purity in yields of 51 - 92 percent for 18 typical representatives.The synthesis succeeds in certain instances where conventional reduction with aqueous sodium sulfite fails and in other instances often is superior.The method is rapid, mild, selective, convenient, and general, although a few limitations are reported.Characterizations of the sulfinic acids are effected by titration with aqueous sodium nitrite, by IR and 1H-NMR spectra, by preparation of either a S-benzylthiuronium salt or a p-nitrobenzyl ester and either by elemental analyses or comparison with reported melting points of the acids and derivatives as appropriate.
149. Notizen zur Synthese von 2-Aminophenylsulfonen
Courtin, Alfred,Tobel, Hans-Rudolf von,Auerbach, Guenther
, p. 1412 - 1419 (2007/10/02)
Syntheses of the alkyl, cycloalkyl and aryl 2-aminophenyl sulfones 10 were achieved by oxidation of the corresponding 2-nitrophenyl sulfides 7 to the 2-nitrophenyl sulfones 9 followed by ethanolic Bechamp-reduction.The sulfides 7 in turn were obtained by either reactions of 2-nitro-thiophenol (8) with the appropriate alkyl and cycloalkyl halides or of 2-chloro-nitrobenzene (5) with the relevant thiols.Condensation of 2-nitrobenzenesulfinic acid (3) with bromoacetic acid in aqueous alkaline solution led - presumably via 2-nitrophenylsulfonylacetic acid (4) - to methyl2-nitrophenyl sulfone (1), reduction of which gave 2-aminophenyl methyl sulfone (2).Treatment of 2-aminothiophenol (11) with t-butyl alcohol in aqueous sulfuric acid gave 2-aminophenyl t-butyl sulfide (12), which was acetylated to o-t-butylthio-acetanilide (13).Oxidation of the latter to o-t-butylsulfonyl-acetanilide (14) followed by hydrolysis led to 2-aminophenyl t-butyl sulfone (15).
