15446-25-0Relevant academic research and scientific papers
Synthesis and Pharmacological Activity of Tris(2-hydroxyethyl)ammonium 4-Chlorophenylsulfonylacetate
Adamovich,Oborina,Mirskova
, p. 701 - 705 (2018)
Methods for the synthesis of 4-chlorophenylsulfonylacetic acid and its tris(2-hydroxyethyl)ammonium salt (“sulfacetamine”) were studied. The results of in vitro and in vivo experiments showed that sulfacetamine possesses high antithrombotic, antioxidant, hypocholesterolemic, immunostimulating, and protective-adaptive activities.
Synthesis of Sulfones via Ru(II)-Catalyzed Sulfination of Boronic Acids
Gulbe, Krista,Turks, Mā ris
, p. 5660 - 5669 (2020/05/19)
Ruthenium(II) complexes catalyze the insertion of sulfur dioxide into (het)aryl and alkenyl boronic acids. The transmetalation-sulfination process proceeds with DABSO in the presence of 5 mol % RuCl2(PPh3)3 in methanol at 100 °C. The intermediate sulfinate salt can be quenched with various electrophiles such as alkyl halides, epoxides, Michael acceptors, and λ3-iodanes in moderate to good yields. The reported sulfone synthesis can be performed either as a direct one-pot or one-pot two-step procedure depending on the reactivity of the electrophile.
Discovery of 4-amino-3-arylsulfoquinolines, a novel non-acetylenic chemotype of metabotropic glutamate 5 (mGlu5) receptor negative allosteric modulators
Galambos, János,Bielik, Attila,Wágner, Gábor,Domány, Gy?rgy,Kóti, János,Béni, Zoltán,Szigetvári, áron,Sánta, Zsuzsanna,Orgován, Zoltán,Bobok, Amrita,Kiss, Béla,Mikó-Bakk, Mónika L.,Vastag, Mónika,Sághy, Katalin,Krasavin, Mikhail,Gál, Krisztina,Greiner, István,Szombathelyi, Zsolt,Keser?, Gy?rgy M.
, p. 240 - 254 (2017/04/10)
Negative allosteric modulators of metabotropic glutamate receptor 5 (mGlu5) showed efficacy in a number of animal models of different CNS diseases including anxiety and depression. Virtually all of the compounds which reached the clinic belong to the same chemotype having an acetylenic linker that connects (hetero)cyclic moieties. Searching for new chemotypes we identified a morpholino-sulfoquinoline derivative (1) by screening our corporate compound deck. The HTS hit showed reasonable affinity and selectivity towards mGlu5 receptors, however, its inferior metabolic stability prevented its testing in?vivo. In a chemical program we aimed to improve the affinity, physicochemical properties and metabolic stability exploring three regions of the hit. Systematic variation of different amines at position 4 (region I) led to the identification of 4-methyl-piperidinyl analogues. Substituents of the quinoline core (region II) and the phenylsulfonyl moiety (region III) were mapped by parallel synthesis. Evaluation of both morpholino- and 4-methyl-piperidinyl-sulfoquinoline libraries of about 270 derivatives revealed beneficial substituent combinations in regions II and III. Blood levels of optimized 4-methyl-piperidinyl-sulfoquinolines, however, were still insufficient for robust in?vivo efficacy. Finally, introducing 4-hydoxymethyl-piperidinyl substituent to region I resulted in new sulfoquinolines with greatly improved solubility and reasonable affinity coupled with affordable metabolic stability. The most promising analogues (24 and 25) showed high blood levels and demonstrated significant efficacy in the experimental model of anxiety.
QUINOLINONE DERIVATIVES FOR USE IN THE TREATMENT OF AN AUTOIMMUNE DISEASE AND/OR AN INFLAMMATORY DISEASE
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Paragraph 0188; 0189, (2014/02/16)
There is provided compounds of formula I, wherein X1 to X4, R1 to R4, Y1, Y2 and L are as defined in the description, and pharmaceutically-acceptable salts thereof, which may be useful in the treatment and/or prophylaxis of autoimmune diseases, inflammatory (e.g. chronic inflammatory) diseases and/or other diseases that may benefit from production of ROS (reactive oxygen species) by a NADPH oxidase complex.
SULFONYL-QUINOLINE DERIVATIVES
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Page/Page column 29, (2009/01/23)
New mGluRl and mGluR5 receptor subtype preferring ligands of formula: (I) and/or salts and/or hydrates and/or solvates thereof, to the processes and intermediates for their preparation, to pharmaceutical compositions containing these compounds and to thei
QUINOLINE DERIVATIVES USEFUL IN THE TREATMENT OF MGLUR5 RECEPTOR-MEDIATED DISORDERS
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Page/Page column 40, (2008/06/13)
Compounds of formula (I): and/or enantiomers and/or racemates and/or diastereomers and/or pharmaceutically acceptable salts thereof formed with acids or bases, to the process for their preparation, to the intermediates of the preparation process, to the p
Reactions of Arylsulphonyl, Arylthio and Acyl Acetates with S-Containing Heterocumulenes
Chatterjee, Swapan K.,Rudorf, Wolf-Dieter
, p. 2916 - 2935 (2007/10/02)
The reaction of arylsulphonyl- or (phenylthio)-acetates 1 with carbon disulphide in a basic medium led to the corresponding ketene dithioacetals 2 in good yields.The o-chloro derivative 1d gave with carbon disulphide various products under different reaction conditions.However, the reaction of 1 with phenyl isothiocyanate primarily resulted in N-substituted pyrimidone derivatives 9, except for 1e which mainly gave S,N-analogues of dithioacetals 10e and 10f. β-Ketoesters 1g, h also reacted with phenyl isothiocyanate to afford 5-acyl-2-thioxo-4-pyrimidones 9g, h.The dependency of the polarisation of the double bond in ketene dithioacetals and their S,N-analogues on acceptor groups was investigated with the help of 13C NMR spectroscopy.
SYNTHESIS OF ORGANOSULFONYLACETIC ACID
Mirskova, A.N.,Kryukova, Yu.I.,Levkovskaya, G.G.,Guseva, S.A.,Voronkov, M.G.
, p. 545 - 550 (2007/10/02)
Alkylsulfonylacetic acids and their esters were obtained by the alcoholysis of alkyl β,β-dichlorovinyl sulfones and the oxidation of alkylthioacetic acids.Arylsulfonylacetic acids were synthesized by the reaction of sodium arenesulfinates with monochloroacetic acid.The optimum conditions for the reaction were obtained.Arylsulfonylacetic esters were obtained by the reaction of monochloroacetic esters with sodium arenesulfinate in DMFA, and their hydrolysis led to the corresponding acids with yields of 65-98percent.Dichloroacetic estersreacts with arenesulfinates, forming di(arylsulfonyl)acetic esters.
ALKYLATION OF ARYLSULFONYLACETIC ESTERS
Levkovskaya, G. G.,Guseva, S. A.,Kryukova, Yu. I.,Mirskova, A. N.,Voronkov, M. G.
, p. 1310 - 1314 (2007/10/02)
The C-alkylation reactions of arylsulfonylacetic esters with alkyl halides in DMFA in the presence of alkali with the reagents in ratios of 1:1.3:1.3 and 1:2.3:2.3 respectively give high yields of the esters of monoalkyl- and dialkyl-substituted arylsulfo
