- Method for synthesizing sulfone compounds under photocatalysis condition
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The invention belongs to the technical field of compound preparation, and particularly relates to a method for synthesizing sulfone compounds under a photocatalysis condition. Aromatic hydrazine and sulfinate are used as raw materials, and under the action of alkali and a solvent, a sulfone compound is generated through reaction under the condition of air or oxygen under the illumination of visible light. According to the method disclosed by the invention, aryl hydrazine is used as an arylation reagent, polyacid salt is used as a catalyst or an organic photosensitizer is used as a catalyst, and the sulfones compound can be efficiently synthesized by coupling with sulfinate under the condition of room temperature through visible light irradiation. The method has good substrate universalityand relatively mild reaction conditions, is not only a substitute for synthesizing sulfone compounds by coupling from simple substrates reported at present, but also broadens the new application of the polyacid salt in the field of photocatalysis.
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Paragraph 0144-0148
(2021/03/31)
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- A Copper(I)-Catalyzed Sulfonylative Hiyama Cross-Coupling
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An air-tolerant Cu-catalyzed sulfonylative Hiyama cross-coupling reaction enabling the formation of diaryl sulfones is described. Starting from aryl silanes, DABSO and aryliodides, the reaction tolerates a large variety of polar functional groups (amines, ketones, esters, aldehydes). Control experiments coupled with DFT calculations shed light on the mechanism, characterized by the formation of a Cu(I)-sulfinate intermediate via fast insertion of a SO2 molecule.
- Adenot, Aurélien,Anthore-Dalion, Lucile,Nicolas, Emmanuel,Berthet, Jean-Claude,Thuéry, Pierre,Cantat, Thibault
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supporting information
p. 18047 - 18053
(2021/11/16)
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- Synthesis of Sulfones and Sulfonyl Derivatives using Sodium (tert-butyldimethylsilyl)oxymethanesulfinate
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The present invention relates to a method for manufacturing a sulfone and sulfonyl derivative compound using sodium (tert-butyldimethylsilyl)oxymethanesulfinate, which is a novel organic sulfin salt, wherein the novel organic sulfin salt has good stability, environmental friendliness and economy, and is easy to handle, and thus significantly reduces the amount of transition metal catalysts and the amount of organic sulfin salts used when introducing aryl or alkenyl. Also, alkylation, arylation, amination, and fluorination are all possible during secondary functionalization. Therefore, the present invention can be usefully used in preparation and mass production of various kinds of sulfones and derivatives thereof including asymmetric sulfone derivatives.
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Paragraph 0704-0710; 0712; 0714-0715; 0717-0720; 0722-0725
(2021/04/29)
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- Silyloxymethanesulfinate as a sulfoxylate equivalent for the modular synthesis of sulfones and sulfonyl derivatives
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An efficient protocol for the modular synthesis of sulfones and sulfonyl derivatives has been developed utilizing sodium tert-butyldimethylsilyloxymethanesulfinate (TBSOMS-Na) as a sulfoxylate (SO22-) equivalent. TBSOMS-Na, easily prepared from the commercial reagents Rongalite and TBSCl, serves as a potent nucleophile in S-alkylation and Cu-catalyzed S-arylation reactions with alkyl and aryl electrophiles. The sulfone products thus obtained can undergo the second bond formation at the sulfur center with various electrophiles without a separate unmasking step to afford sulfones and sulfonyl derivatives such as sulfonamides and sulfonyl fluorides.
- Kim, Dae-Kwon,Um, Hyun-Suk,Park, Hoyoon,Kim, Seonwoo,Choi, Jin,Lee, Chulbom
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p. 13071 - 13078
(2021/01/09)
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- SUBSTITUTED PHENYL SULFONYL PHENYL TRIAZOLE THIONES AND USES THEREOF
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The present disclosure relates to substituted phenyl sulfonyl phenyl triazole thiones, pharmaceutical compositions containing them, and methods of using them.
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- METHOD OF TREATING A CONDITION ASSOCIATED WITH NEURODEGENERATION USING INHIBITORS OF OAT3
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The present disclosure relates to therapeutic agents that may be useful in treatment and prophylaxis of neurodegenerative disorders and/or neural inflammation.
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- Crystallographic and SAR analyses reveal the high requirements needed to selectively and potently inhibit SIRT2 deacetylase and decanoylase
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A high-quality X-ray crystal structure reveals the mechanism of compound 1a inhibiting SIRT2 deacetylase and decanoylase. Structure-activity relationship (SAR) analysis of the synthesized derivatives of 1a reveals the high requirements needed for selectiv
- Yang, Ling-Ling,Xu, Wei,Yan, Jie,Su, Hui-Lin,Yuan, Chen,Li, Chao,Zhang, Xing,Yu, Zhu-Jun,Yan, Yu-Hang,Yu, Yamei,Chen, Qiang,Wang, Zhouyu,Li, Lin,Qian, Shan,Li, Guo-Bo
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supporting information
p. 164 - 168
(2019/01/30)
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- SMALL MOLECULE ACTIVATORS OF NICOTINAMIDE PHOSPHORIBOSYLTRANSFERASE (NAMPT) AND USES THEREOF
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Provided herein are small molecule activators of Nicotinamide Phosphoribosyltransferase (NAMPT), compositions comprising the compounds, and methods of using the compounds and compositions.
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Paragraph 00631; 00661
(2018/08/03)
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- Visible-Light Photoredox/Nickel Dual Catalysis for the Cross-Coupling of Sulfinic Acid Salts with Aryl Iodides
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An efficient cross-coupling of sodium or lithium sulfinates with aryl iodides, using a combination of nickel and photoredox catalysis, is described. The dual catalyst system enables a versatile synthesis of aryl sulfones at room temperature in good yields and displays a broad functional group compatibility. The potential utility of this method in the late-stage diversification of complex molecules and in the conversion of organolithium reagents and sulfur dioxide into sulfones is demonstrated.
- Liu, Nai-Wei,Hofman, Kamil,Herbert, André,Manolikakes, Georg
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supporting information
p. 760 - 763
(2018/02/09)
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- METHODS OF INHIBITING BACTERIAL VIRULENCE AND COMPOUNDS RELATING THERETO
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The present invention relates to compounds and methods for the treatment of bacterial infections. Because their mechanism of action does not involve killing of bacteria or inhibiting their growth, the potential for these compounds to induce drug resistance in bacteria is minimized. Through inhibiting bacterial virulence, the present invention provides a novel means of treating bacterial infections.
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Paragraph 0211
(2017/01/31)
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- Copper(i)-catalyzed sulfonylative Suzuki-Miyaura cross-coupling
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Using a simple copper(i) catalyst has allowed a high yielding sulfonylative-Suzuki-Miyaura cross-coupling reaction to be developed. The process provides a single step route to diaryl sulfones from the direct combination of aryl boronic acids, sulfur dioxide and aryl iodides, and represents the first sulfonylative variant of a classic cross-coupling reaction. Sulfur dioxide is delivered from the surrogate reagent, DABSO. Variation of the reaction conditions allowed interruption of the sulfonylative-Suzuki coupling, resulting in the formation of a presumed Cu-sulfinate intermediate. These sulfinates could be trapped as their sodium salts and treated with electrophiles to allow access to arylalkyl sulfones, β-hydroxyl sulfones, sulfonamides and sulfonyl fluorides.
- Chen, Yiding,Willis, Michael C.
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p. 3249 - 3253
(2017/04/04)
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- Triflic acid–catalyzed rearrangement of unalkylated benzene sulfonanilides
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ABSTRACT: Previous work has demonstrated that alkylated benzene sulfonanilides undergo sulfuric acid (98%)–catalyzed rearrangement to alkylamino diaryl sulfones. Similar treatment of their unalkylated analogs typically leads only to hydrolysis. Surprisingly, when the unalkylated benzene sulfonanilides react with triflic acid, rearrangement to sulfones does occur.
- Newcomer, Rebecca,McKee, James,Zanger, Murray
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p. 949 - 955
(2016/07/12)
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- Discovery of potent and efficacious urea-containing nicotinamide phosphoribosyltransferase (NAMPT) inhibitors with reduced CYP2C9 inhibition properties
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Potent, reversible inhibition of the cytochrome P450 CYP2C9 isoform was observed in a series of urea-containing nicotinamide phosphoribosyltransferase (NAMPT) inhibitors. This unwanted property was successfully removed from the described inhibitors throug
- Gunzner-Toste, Janet,Zhao, Guiling,Bauer, Paul,Baumeister, Timm,Buckmelter, Alexandre J.,Caligiuri, Maureen,Clodfelter, Karl H.,Fu, Bang,Han, Bingsong,Ho, Yen-Ching,Kley, Nikolai,Liang, Xiaorong,Liederer, Bianca M.,Lin, Jian,Mukadam, Sophie,O'Brien, Thomas,Oh, Angela,Reynolds, Dominic J.,Sharma, Geeta,Skelton, Nicholas,Smith, Chase C.,Sodhi, Jasleen,Wang, Weiru,Wang, Zhongguo,Xiao, Yang,Yuen, Po-Wai,Zak, Mark,Zhang, Lei,Zheng, Xiaozhang,Bair, Kenneth W.,Dragovich, Peter S.
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p. 3531 - 3538
(2013/07/28)
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- Synthesis of substituted diphenyl sulfones and their structure-activity relationship with the antagonism of 5-HT6 receptors
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Substituted diphenyl sulfones (10a-n) were synthesised, and the structures were confirmed by NMR, LC-MS and X-ray crystallography. Their antagonistic activities towards 5-HT6 receptor were assessed in a cell-based functional assay. Diphenyl sulfone 10a, in spite of being the smallest and simplest known sulfonyl-containing 5-HT6R antagonist, showed a strong potency (Ki = 1.6 μM). Its derivative with a methylamine substituent, 10g (N-methyl-2-(phenylsulfonyl)aniline), was ~66-times as active as diphenyl sulfone (Ki = 24.3 nM). Addition of a piperazinyl moiety in the para-position relative to the sulfonyl group in compound 10m (N-methyl-2-(phenylsulfonyl)-5-piperazin-1-ylaniline) led to a further 150-fold increase in potency (Ki = 0.16 nM) to block the serotonin-induced response of HEK-293 cells that were stably transfected with the human recombinant 5-HT6 receptor.
- Ivachtchenko, Alexandre,Golovina, Elena,Kadieva, Madina,Mitkin, Oleg,Tkachenko, Sergei,Okun, Ilya
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p. 4614 - 4627
(2013/07/26)
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- PROCESS FOR THE PRODUCTION OF A SULFONE MONOMER
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The present invention provides an economic and environmentally friendly method for the preparation of polymer grade 4,4'-dichlorodiphenyl sulfone which is substantially free of 2,4' and 3,4'-isomers of dichlorodiphenyl sulfone with yield of over 90%, with substantially reduced reaction times without the use of impregnated catalysts. Further no toxic byproducts such as dimethyl pyrosulfate are formed thereby reducing the load on effluent treatment with the added advantage of substantially recycling the reactants and byproducts. Further the present invention discloses a process is disclosed in which isomeric mixture of 4,4'-, 3,4'-, and 2,4'-dichlorodiphenyl sulfone produced during the preparation of 4,4'-dichlorodiphenyl sulfone is converted to value added products such as diphenyl sulfone, 2,4'- dihydroxydiphenyl sulfone, 4,4'-dihydroxydiphenyl sulfone and 2-aminodiphenyl sulfone.
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- SOLUBLE EPOXIDE HYDROLASE INHIBITORS
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Disclosed are sulfone compounds and compositions that inhibit soluble epoxide hydrolase (sEH), methods for preparing the compounds and compositions, and methods for treating patients with such compounds and compositions. The compounds, compositions, and m
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Page/Page column 47
(2008/06/13)
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- ARYLSULFONYLNAPHTHALENE DERIVATIVES AS 5HT2A ANTAGONISTS
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Compounds of formula (I) are potent and selective 5-HT2A antagonists, useful in treatment of a variety of adverse conditions of the CNS.
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Page/Page column 26-27
(2008/06/13)
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- ARYLSULFONYL BENZOFUSED HETEROCYCLES AS 5-HT2A ANTAGONISTS
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Compounds of formula (I): are potent and selective antagonists of the 5-HT2A receptor, and hence are useful in treatment of various CNS disorders.
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- Regioselectivity control of radiation-induced reaction: Electron beam-induced Fries rearrangement of sulfonamide within a β-cyclodextrin inclusion complex
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EB (electron beam) irradiation of sulfonamide within a β-cyclodextrin (β-CD) inclusion complex in the solid state induced the solvent-free Fries rearrangement, which proceeded at a shorter reaction time with reversed regioselectivity by inclusion into the β-CD, compared with that of sulfonamide crystals; the β-CD as a restricted nanospace had a large effect on the reactivity and regioselectivity of the solvent-free EB-Fries rearrangement. The Royal Society of Chemistry 2006.
- Kato, Jun,Kakehata, Hiroyuki,Maekawa, Yasunari,Yamashita, Takashi
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p. 4498 - 4500
(2008/09/19)
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- Electron beam-induced fries rearrangement of sulfonamide and sulfonate crystals
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The electron beam (EB) sensitivity of sulfonic acid derivatives in the crystalline state was much higher than that of the corresponding carboxylic acid derivatives, which was distinct from the results using other energy sources such as heat and UV; especially, sulfonamide derivatives could undergo the chemoselective Fries rearrangement to give ortho and para products in the ratio of ca. 7/3 without the meta isomer. Copyright
- Kato, Jun,Maekawa, Yasunari,Yoshida, Masaru
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p. 266 - 267
(2007/10/03)
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- Bicyclic heterocycles, the preparation thereof, and their use as pharmaceuticals
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The present invention relates to 5-membered heterocyclic condensed benzoderivatives of formula wherein Ra to Rc, A, X and Y are defined as in claim 1, the tautomers, stereoisomers, mixtures thereof and the salts thereof, particularly the physiologically acceptable salts thereof with inorganic or organic acids or bases which have valuable properties. The compounds of the above formula I wherein Rc denotes a cyano group are valuable intermediates for preparing the other compounds of formula I, and the compounds of the above formula I wherein Rc denotes one of the following amidino groups and the tautomers and stereoisomers thereof have valuable pharmacological properties, particularly an antithrombotic activity.
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- ISOXAZOLINE, ISOTHIAZOLINE AND PYRAZOLINE FACTOR XA INHIBITORS
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Isoxazolines, isothiazolines and pyrazolines which are inhibitors of Factor Xa, pharmaceutical compositions containing these compounds, and methods of using these compounds as anticoagulant agents for treatment and prevention of thromboembolic disorders. The compounds can be represented by the formula: STR1 where X is O, S or NR 15.
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- 1,2-Diarylpyrroles as potent and selective inhibitors of cyclooxygenase- 2
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Series of 1,2-diarylpyrroles has been synthesized and found to contain very potent and selective inhibitors of the human cyclooxygenase-2 (COX-2) enzyme. The paper describes short and practical syntheses of the target molecules utilizing the Paal-Knorr reaction. Electrophilic substitution on 1 proceeds in a regioselective fashion, and the method was used to generate a number of tetrasubstituted pyrroles. Detailed SAR on the series has been studied by modifications of the aryl rings and the substituents in the pyrrole ring. Diarylpyrrole 1 is a very potent (COX-2, IC50 = 60 nm) and selective (COX-1/COX-2 = > 1700) inhibitor whereas the isomeric 2 is completely inactive against COX-2. Modifications of the substituents on the fluorophenyl ring in 1 yields very potent inhibitors of COX-2 (IC50 = 40- 80 nm) with excellent selectivity(1200 to >2500) vs COX-1, Analog 20 containing a sulfonamide group is an excellent inhibitor of COX-2 with an IC50 of 14 nm. Tetrasubstituted pyrroles containing groups such as COCF3, SO2CF3, or CH2OAr at position 3 in the pyrrole ring give excellent inhibitors (COX-2, IC50 = 30-120 nm). In vivo testing in the carrageenan- induced paw edema model in the rat establishes that the 1,2-diarylpyrroles are orally active antiinflammatory agents. Compound 3 is the most potent inhibitor of edema with an ED50 of 4.7 mpk.
- Khanna, Ish K.,Weier, Richard M.,Yu, Yi,Collins, Paul W.,Miyashiro, Julie M.,Koboldt, Carol M.,Veenhuizen, Amy W.,Currie, Jerry L.,Seibert, Karen,Isakson, Peter C.
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p. 1619 - 1633
(2007/10/03)
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- Effect of cyclodextrin encapsulation on photo-fries rearrangement of benzensulphonanilide
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Photolysis of benzenesulphonanilide upon cyclodextrin encapsulation in solid phase yields exclusively 2-aminodiphenyl sulphone.
- Pitchumani,Manickam,Srinivasan
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p. 2975 - 2978
(2007/10/02)
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- Antiproliferative cyclic compounds
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A compound of formula (I) capable of inhibiting thymidylate synthase, a method for making such and a therapeutic process utilizing the compound of formula (I).
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- Syntheses of Some Alkyl-, Cycloalkyl-, and Aryl-(4-aminophenyl)-sulfones
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Syntheses of (4-aminophenyl)-alkyl, -cycloalkyl and -aryl sulfones 2 were achieved both by alkylation of 4-(acetylamino)-benzenesulfinic acid (7) to the corresponding acetanilides 9 followed by hydrolysis and by oxidation of the appropriate (4-nitrophenyl)-sulfides 11 to (4-nitrophenyl)-sulfones 1 with subsequent Bechamp reduction.
- Courtin, Alfred
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p. 1046 - 1052
(2007/10/02)
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