- NOVEL PHENYLSULFONYL OXAZOLE DERIVATIVE AND USE THEREOF
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The present invention relates to a novel phenylsulfonyl oxazole derivative and a use thereof and specifically, to a compound represented by Chemical Formula 1 in the present specification or a pharmaceutically acceptable salt thereof, and to a use thereof for prevention, treatment, or improvement of neurodegenerative disease.
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Paragraph 0130-0133
(2021/03/13)
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- Synthesis, characterization and antioxidant activity of bis (arylsulfonylmethyl/arylaminosulfonylmethylazolyl) pyridines
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A new class of bis(arylsulfonylmethylazolyl)pyridines and bis(arylaminosulfonylmethyl-azolyl)pyridines were synthesized from the synthetic intermediates methyl arylsulfonylacetic acid hydrazide and methyl arylaminosulfonylacetic acid hydrazide adopting a green methodology-ultrasonication. All the synthesized compounds were resulted in higher yield and in shorter reaction times. The spectral parameters such as IR, 1H NMR, 13C NMR, mass and microanalyzes were used to determine the structures of all the synthesized compounds and were assayed for antioxidant activity. The bis(arylaminosulfonylmethylazolyl)pyridines showed higher radical scavenging activity than the bis(arylsulfonylmethylazolyl)pyridines. Besides, unsubstituted, and methyl substituted compounds exhibited greater activity. Among all the tested compounds 8b and 11b were identified as potential antioxidants.
- Gunthanakkala, Anil Kumar,Mangali, Madhu Sekhar,Venkatapuram, Padmavathi,Adivireddy, Padmaja
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p. 4164 - 4174
(2020/09/07)
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- Synthesis of Sulfones via Ru(II)-Catalyzed Sulfination of Boronic Acids
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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.
- Gulbe, Krista,Turks, Mā ris
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p. 5660 - 5669
(2020/05/19)
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- AUTOPHAGY ENHANCER AND USE THEREOF
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Provided are a compound of chemical formula 1 or 2 and a use thereof. The compound can be advantageously used in the prevention or treatment of metabolic diseases including type 2 diabetes, insulin resistance, or obesity, on the basis of a mechanism of autophagy activation through the promotion of lysosome production.
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- Discovery of 4-amino-3-arylsulfoquinolines, a novel non-acetylenic chemotype of metabotropic glutamate 5 (mGlu5) receptor negative allosteric modulators
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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.
- 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.
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p. 240 - 254
(2017/04/10)
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- Application of sodium titanate nanotubes doped with vanadium (VNaTNT) as a heterogeneous catalyst for oxidation of sulfides at room temperature
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A heterogeneous titanate nanotube (TNT) catalyst containing TiO2, Na, and V has been synthesized and used in the chemoselective oxidation of sulfides to the corresponding sulfoxides in the presence of 30% H2O2 in water. Some of the advantages of our method include excellent yields, heterogeneous conditions, simplicity, compatibility with a variety of functionalities, and ease of isolation of the products. Fourier transform infrared spectroscopy, X-ray diffraction, scanning electron microscopy, transmission electron microscopy, and N2 adsorption were used for structural and textural characterization of the catalyst (VNaTNT).
- Dadvar, Mohammad Ali,Fazaeli, Razieh
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p. 494 - 501
(2016/04/20)
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- Imidazolium perrhenate ionic liquids as efficient catalysts for the selective oxidation of sulfides to sulfones
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A series of imidazolium perrhenate ionic liquids (IPILs) have been synthesized and used as efficient catalysts for the oxidation of sulfides to sulfones with aqueous hydrogen peroxide under mild conditions. Various sulfones are obtained in good to excellent yields. IPILs are stable and can be reused at least ten times without detectable activity loss. Furthermore, this system provides a reasonably environmentally benign chemical process in terms of potential industrial application.
- Zhang, Bo,Li, Su,Yue, Shuang,Cokoja, Mirza,Zhou, Ming-Dong,Zang, Shu-Liang,Kühn, Fritz E.
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p. 108 - 112
(2013/10/01)
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- Nano-rod catalysts: Building MOF bottles (MIL-101 family as heterogeneous single-site catalysts) around vanadium oxide ships
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Porous materials based on chromium (III) terephthalate metal organic frameworks (Cr-MIL(101)) and their new composites with vanadium oxide has emerged as a potential catalyst because of its high specific surface area, tunable pore size, and unique structure. The structural and textural characterization of V@MIL(101) were done using FTIR, X-ray diffraction, N 2 adsorption-desorption, and TEM. XRD and adsorption-desorption analysis shows that the mesostructure of MIL-101 remains intact after vanadium oxide modifications, while spectral technique show the successful immobilizing of the neat vanadium oxide inside the MIL-101 cavities. These new catalysts were found to be highly effective for selective oxidation of sulfides to sulfoxides and sulfones with H2O2 at room temperature and the 4.2% V@MIL(101) catalyst showed the highest activity. The PW12@MCF im heterogeneous system showed high catalytic oxidative activity in the treatment of commodity gasoline.
- Fazaeli, Razieh,Aliyan, Hamid,Moghadam, Majid,Masoudinia, Mona
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- Host (aluminum incorporated mesocellulous silica foam (Al-MCF))-guest (tungsten polyoxometalate) nanocomposite material: An efficient and reusable catalyst for selective oxidation of sulfides to sulfoxides and sulfones
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A green, efficient and selective approach for the oxidation of sulfides to sulfoxides and sulfones with H2O2 at room temperature is reported. The reaction is performed in the presence of tungstophosphoric acid (PW12) supported on an aluminum incorporated mesocellulous silica foam (Al-MCF) (via both: the impregnation and encapsulation methods), as heterogeneous and reusable catalysts. The structural and textural characterizations of these catalysts were done using FTIR, X-ray diffraction, N2 adsorption-desorption and TEM.
- Fazaeli, Razieh,Aliyan, Hamid,Ahmadi, Mohammad Ali,Hashemian, Saeedeh
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- TiCl4 hiocarbonyls and oxidation of sulfides in the presence of H2O2
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H2O2 in combination with TiCl4 proved to be a highly reactive reagent system for the desulfurization of thioamide and thioketone derivatives in excellent yields and short reaction times with high purity. Sulfides were also found to undergo oxidation to sulfones under similar reaction conditions. In most cases, these reactions are highly selective, simple, and clean, affording products in high yields and purity.
- Bahrami, Kiumars,Khodaei, Mohammad M.,Shakibaian, Vida,Khaledian, Donya,Yousefi, Behrooz H.
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experimental part
p. 155 - 163
(2012/06/01)
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- Switching pathways: Room-temperature neutral solvolysis and substitution of amides
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Stick or twist: By introducing steric hindrance at the nitrogen atom, stable linear amides bearing an electron-withdrawing α-substituent (Z=Ar, PhSO2, P(O)(OR)2, CN, or CO2R) can be induced to undergo solvolysis and substitution reactions through an elimination-addition mechanism (see picture). Key to this process is a low barrier to rotation around the amide bond and the α-substituentZ. Copyright
- Hutchby, Marc,Houlden, Chris E.,Haddow, Mairi F.,Tyler, Simon N. G.,Lloyd-Jones, Guy C.,Booker-Milburn, Kevin I.
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p. 548 - 551
(2012/02/04)
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- Cyanuric chloride as promoter for the oxidation of sulfides and deoxygenation of sulfoxides
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This Letter discusses the use of cyanuric chloride as an efficient promoter for the chemoselective oxidation of sulfides to the corresponding sulfones in the presence of H2O2 as the terminal oxidant. Sulfoxides were also found to undergo deoxygenation to sulfides with cyanuric chloride and potassium iodide system. The reaction is broad in scope and easy to perform.
- Bahrami, Kiumars,Khodaei, Mohammad M.,Sohrabnezhad, Samira
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experimental part
p. 6420 - 6423
(2011/12/21)
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- TAPC-promoted oxidation of sulfides and deoxygenation of sulfoxides
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Figure presented. 1,3,5-Triazo-2,4,6-triphosphorine-2,2,4,4,6,6- tetrachloride (TAPC) was found to be an efficient promoter for the oxidation of sulfides and deoxygenation of sulfoxides. Excellent yields, short reaction time, easy and quick isolation of the products, solvent-free process, and excellent chemoselectivity are the main advantages of this procedure.
- Bahrami, Kiumars,Khodaei, Mohammad M.,Sheikh Arabi, Mehdi
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supporting information; experimental part
p. 6208 - 6213
(2010/11/04)
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- Synthesis, antimicrobial and cytotoxic activities of 1,3,4-oxadiazoles, 1,3,4-thiadiazoles and 1,2,4-triazoles
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A new class of 1,3,4-oxadiazoles were prepared from acid hydrazides on treatment with different carboxylic acids in the presence of phosphorus oxychloride. Interconversion of oxadiazoles to thiadiazoles and triazoles was carried out with appropriate reagents. The antimicrobial and cytotoxic activities of compounds 7a-d to 12a-d were tested. Compounds 10d and 12d showed pronounced antimicrobial activity. Further, compound 10d exhibited maximum cytotoxicity.
- Padmavathi,Sudhakar Reddy,Padmaja,Kondaiah,Ali-Shazia
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experimental part
p. 2106 - 2112
(2009/09/25)
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- Synthesis of thiadiazoles, triazoles and oxadiazoles from sulfonyl acetic acids via a common route
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A new class of five membered heterocycles, thiadiazoles, triazoles and oxadiazoles were prepared from sulfonyl acetic acids via acid hydrazides.
- Padmavathi, Venkatapuram,Thriveni, Pinnu,Reddy, Boggu Jagan Mohan,Padmaja, Adivireddy
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p. 113 - 116
(2007/10/03)
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- Sulfonyl acetic acids - Source for substituted 2-oxazolines
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A new class of 2-oxazolines have been prepared from N-(2-chloroethyl) sulfonamides by base promoted cyclization with NaH in THF. All the compounds are characterized by IR and 1H NMR spectra.
- Padmavathi,Reddy, B. Chandra Obula,Subbaiah, D. R. C. Venkata,Padmaja
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p. 2456 - 2458
(2007/10/03)
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- Flash vacuum pyrolysis of stabilised phosphorus ylides. Part 15. Generation of alkoxycarbonyl(sulfenyl)carbenes and their intramolecular insertion to give alkenyl sulfides
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A range of 18 alkoxycarbonyl sulfinyl phosphorus ylides 9 have been prepared and their behaviour upon flash vacuum pyrolysis (FVP) at 600 deg C examined. For R1 = H, Me and Et they lose Ph3PO and in some cases Ph3P to give mixtures of products including the alkenyl sulfides 10, the sulfides 11, the disulfides 12 and the thioesters 14. The alkenyl sulfides 10 most likely arise from intramolecular insertion of the alkoxycarbonyl sulfenyl carbenes resulting from loss off Ph3PO to produce β-lactones which then lose CO2 and this is supported by the results from 13C labelled ylides. Possible mechanisms for the formation of 11 and 14 are also presented and the feasibility of various steps has been examined by preparation and pyrolysis of the proposed intermediates. In contrast, pyrolysis of the ylides 9 where R1 = Ph and the tert-butoxycarbonyl ylides 30 leads mainly to complete fragmentation with loss of Ph3PO and benzyl alcohol or 2-methylpropan-2-ol and does not give any useful sulfur-containing products. Four alkoxy-carbonyl sulfonyl diazo compounds 33 have been prepared and in three cases they give the alkenyl sulfones 34 upon FVP at 400 deg C, probably by an intramolecular insertion and decarboxylation process analogous to the formation of 10 from 9. On the other hand the alkoxycarbonyl carbenes produced by FVP of the amino acid-derived diazo compounds 35 undergo alternative proocesses with no sign of β-lactone formation. Fully assigned 13C NMR data are presented for 13 of the ylides.
- Aitken, R. Alan,Armstrong, Jill M.,Drysdale, Martin J.,Ross, Fiona C.,Ryan, Bruce M.
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p. 593 - 604
(2007/10/03)
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- Solid state oxidation of aromatic sulfides to corresponding phenyl and p-tolyl sulfoxides and sulone using oxone
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Phenyl and p-tolyl sulfides 1 can be selectively oxidised to the corresponding sulfoxides 2 or sulfones 3 in solid state condition using oxone. The advantages of this method are the use of cheap and safe reagents, high yield and simple operating conditions.
- Hajipour, A. R.
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p. 1069 - 1070
(2007/10/03)
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- Effect of added benzoic acid on the phase-transfer catalysed permanganate oxidation of organosulfur compounds
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The addition of benzoic acid in the oxidation of a range of sulfides and thiazolidinethiones using KMnO4 under phase-transfer conditions provides a convenient and high yielding procedure for formation of the corresponding sulfones, thiazolidinones and thiazolidinone S,S-dioxides.
- Aitken, R. Alan,Mesher, Shaun T. E.,Ross, Fiona C.,Ryan, Bruce M.
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p. 787 - 791
(2007/10/03)
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- Reactions of Arylsulphonyl, Arylthio and Acyl Acetates with S-Containing Heterocumulenes
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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.
- Chatterjee, Swapan K.,Rudorf, Wolf-Dieter
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p. 2916 - 2935
(2007/10/02)
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- Synthesis of the 6-Methylencarboxylic Acid Derivatives of Testosterone and Progesterone
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The methyl 6β-(phenylsulfonyl)acetate and methyl 6β-(methylsulfonyl)acetate derivatives 8 and 10, respectively, of testosterone and of progesterone (9 and 11, respectively) were synthesized by allylic alkylation of the corresponding ?-allylpalladium chloride complexes 3 and 4.Chromatographic separation of the reaction mixtures yields as main products 8a and 9a with S configuration at the new asymmetric center.By-products 8b and 9b have R configuration.The corresponding by-products were not found in reaction mixtures of 10 and 11.The by-products 9c and 11c with α-configuration at C-17 (isoprogesterone derivatives) were isolated from the corresponding reaction mixtures.Alkaline treatment of the main products leads to the 6-methylenecarboxylic acid derivatives as a result of elimination and saponification: 8a and 11a gave 16 and 17.Base-catalyzed elimination of 9a yields the α,β-unsaturated methyl ester 19.NMR spectroscopic investigations (NOE, NOESY) of 19 support the predicted E configuration.
- Handschuh, Dieter,Voelter, Wolfgang
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p. 1007 - 1016
(2007/10/02)
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- OXIDATION OF SULFIDES BY IODYLARENES IN THE PRESENCE OF VANADYL ACETONYLACETONATE AS A CATALYST
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Key words: Sulfide oxidation; sulfoxide; iodylarene; vanadyl acetylacetonate.Iodylbenzene is a poor oxidant of sulfur, but in the presence of vanadyl acetylacetonate, sulfides are converted into sulfoxides, sulfones and S-dealkylated products.To improve the selectivity and the yield of this reaction, different substituted iodylarenes are used.The N-(paraiodylphenyl) palmitoylamid is a promising oxidant for synthetic purposes.
- Barret, R.,Pautet, F.,Bordat, P.,Tinland, B.,Daudon, M.
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- Organic Syntheses without Solvent: Preparation of Sulfones and Dithioacetals
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Sulfones are prepared by alkylation of sulfinate salts under solid-liquid phase-transfer catalysis without solvent; dithioacetals are obtained by heterogeneous uncatalyzed reactions of potassium arenethiolates and gem-dihaloalkanes.In both cases, the yields are high and the reaction conditions are mild.Some limitations are given.
- Bram, Georges,Loupy, Andre,Roux-Schmitt, Marie Claude,Sansoulet, Jean,Strzalko, Tekla,Seyden-Penne, Jacqueline
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- NUCLEOPHILIC REACTIONS AT A VINYLIC CENTER. XVIII. REACTIVITY OF Z-α,β-DIBROMOVINYL PHENYL SULFONE AND THE "ELEMENT EFFECT" IN α,β-DIHALOGENOVINYL SULFONES
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The reaction of Z-α,β-dibromovinyl phenyl sulfone PhSO2CBr=CHBr with sodium methoxide and substituted thiophenolates in methanol was investigated.With sodium methoxide the product from substitution of the bromine at the β position followed by the addition of methanol PhSO2CHBrCH(OMe)2 is formed.With sodium thiophenolates both PhSO2CBr=CHBr and other α,β-dihalogenovinyl sulfones react with substitution of both halogen atoms, leading to 1-phenylsulfonyl-1,2-bis-(arylthio)ethenes PhSO2C(SAr)=CHSAr, when a twofold excess of the nucleophile is used, but only the halogen atom at the β position is substituted when the reagents are in an equimolar ratio.The reasons for the different directions in the reaction of α,β-dihalogenovinyl sulfones with nucleophiles are considered, the kinetics of the reaction are studied, and the "element effect" is discussed.
- Shainyan, B. A.,Mirskova, A. N.,Bel'skii, V. K.
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p. 1727 - 1736
(2007/10/02)
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- NUCLEOPHILIC REACTIONS AT A VINYL CENTER. XIII. REACTION OF β,β-DIBROMOVINYL PHENYL SULFONE WITH SODIUM IODIDE AND THE REACTIVITY OF β,β-DIIODOVINYL PHENYL SULFONE
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β-Bromo-β-iodovinyl phenyl sulfone and β,β-diiodovinyl phenyl sulfone were obtained by the reaction of β,β-dibromovinyl phenyl sulfone with sodium iodide in acetone.The reactivity of β,β-diiodovinyl phenyl sulfone in reactions with sodium methoxide and thiophenolates was studied.A comparison was made of the relative reactivities of the various β,β-dihalogenovinyl sulfones (Hlg = Cl, Br, I) in nucleophilic vinylic substitution within the scope of the elimination-addition and direct substitution mechanisms.
- Shainyan, B. A.,Mirskova, A. N.
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p. 1989 - 1993
(2007/10/02)
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- NUCLEOPHILIC REACTIONS AT VINYL CENTER. VIII. SYNTHESIS AND PROPERTIES OF β,β-DIBROMOVINYL PHENYL SULFONE
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The radical reaction of tribromoethylene with thiophenol was investigated.In addition to the main product, β,β-dibromovinyl phenyl sulfide, 15-30percent (depending on the conditions) of a mixture of isomeric β-bromovinyl phenyl sulfides is formed. β,β-Dibromovinyl phenyl sulfone was obtained by the oxidation of dibromovinyl phenyl sulfide, and it readily enters into nucleophilic vinyl substitution of both bromine atoms.During comparison of its reactivity with the reactivity of the previously investigated dichlorovinyl phenyl sulfone a clearly defined "element-effect" was detected, indicating cleavage of the C-Hlg bond at the rate-determining stage.
- Shainyan, B. A.,Mirskova, A. N.
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p. 443 - 446
(2007/10/02)
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- Applicability of Hammett Equation to Kinetics of Acid-catalysed Esterification of ortho-Substituted Phenoxyacetic, Phenylmercaptoacetic and Phenylsulphonylacetic Acids by Methanol
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Correlation analysis of the title rate data shows that the steric effects of ortho-substituents are absent at the reaction centre.
- Baliah, V.,Gurumurthy, R.
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p. 257 - 258
(2007/10/02)
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- Applicability of Hammett Equation to Kinetics of Acid-catalysed Esterification of meta- and para-Substituted Phenylmercaptoacetic and Phenylsulphonylacetic Acids with Methanol
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Rate constants have been determined for the acid-catalysed esterification of meta- and para-substituted phenylmercaptoacetic and phenylsulphonylacetic acids with methanol using hydrogen chloride as catalyst.The lower reactivities of phenylmercaptoacetic acids compared to those of the corresponding phenoxyacetic acids are discussed.
- Baliah, V.,Gurumurthy, R.
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p. 725 - 726
(2007/10/02)
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