121-51-7Relevant academic research and scientific papers
Aromatic Chlorosulfonylation by Photoredox Catalysis
Májek, Michal,Neumeier, Michael,Jacobi von Wangelin, Axel
, p. 151 - 155 (2017)
Visible-light photoredox catalysis enables the efficient synthesis of arenesulfonyl chlorides from anilines. The new protocol involves the convenient in situ preparation of arenediazonium salts (from anilines) and the reactive gases SO2and HCl (from aqueous SOCl2). The photocatalytic chlorosulfonylation operates at mild conditions (room temperature, acetonitrile/water) with low catalyst loading. Various functional groups are tolerated (e.g., halides, azides, nitro groups, CF3, SF5, esters, heteroarenes). Theoretical and experimental studies support a photoredox-catalysis mechanism.
Proline-Based Allosteric Inhibitors of Zika and Dengue Virus NS2B/NS3 Proteases
Millies, Benedikt,Von Hammerstein, Franziska,Gellert, Andrea,Hammerschmidt, Stefan,Barthels, Fabian,G?ppel, Ulrike,Immerheiser, Melissa,Elgner, Fabian,Jung, Nathalie,Basic, Michael,Kersten, Christian,Kiefer, Werner,Bodem, Jochen,Hildt, Eberhard,Windbergs, Maike,Hellmich, Ute A.,Schirmeister, Tanja
, p. 11359 - 11382 (2019)
The NS2B/NS3 serine proteases of the Zika and Dengue flaviviruses are attractive targets for the development of antiviral drugs. We report the synthesis and evaluation of a new, proline-based compound class that displays allosteric inhibition of both proteases. The structural features relevant for protease binding and inhibition were determined to establish them as new lead compounds for flaviviral inhibitors. Based on our structure-activity relationship studies, the molecules were further optimized, leading to inhibitors with submicromolar IC50 values and improved lipophilic ligand efficiency. The allosteric binding site in the proteases was probed using mutagenesis and covalent modification of the obtained cysteine mutants with maleimides, followed by computational elucidation of the possible binding modes. In infected cells, antiviral activity against Dengue virus serotype 2 using prodrugs of the inhibitors was observed. In summary, a novel inhibitor scaffold targeting an allosteric site shared between flaviviral NS2B/NS3 proteases is presented whose efficacy is demonstrated in vitro and in cellulo.
Preparation method of substituted benzene sulfonyl chloride
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Paragraph 0055-0058, (2021/05/08)
The invention provides a preparation method of substituted benzene sulfonyl chloride, which comprises the following steps: carrying out diazotization reaction on an aniline compound with a structure as shown in a formula I to obtain fluoboric acid diazonium salt with a structure as shown in a formula II; obtaining substituted benzene sulfonyl chloride with a structure as shown in a formula III from the fluoboric acid diazonium salt with the structure as shown in the formula II; wherein R is selected from any one of ortho-chlorine, bromine, methyl, chloromethyl, bromomethyl, nitro, cyano, acetyl, meta-chlorine, bromine, methyl, chloromethyl, bromomethyl, nitro, cyano, acetyl, para-chlorine, bromine, methyl, chloromethyl, bromomethyl, nitro, cyano and acetyl. The preparation method of the substituted benzene sulfonyl chloride provided by the invention is simple in reaction process, easy to operate, ideal in effect and suitable for industrial production.
Facile synthesis of sulfonyl chlorides/bromides from sulfonyl hydrazides
Chen, Rongxiang,Xu, Shaohong,Shen, Fumin,Xu, Canran,Wang, Kaikai,Wang, Zhanyong,Liu, Lantao
, (2021/09/20)
A simple and rapid method for efficient synthesis of sulfonyl chlorides/bromides from sulfonyl hydrazide with NXS (X = Cl or Br) and late-stage conversion to several other functional groups was described. A variety of nucleophiles could be engaged in this transformation, thus permitting the synthesis of complex sulfonamides and sulfonates. In most cases, these reactions are highly selective, simple, and clean, affording products at excellent yields.
Preparation method of dye intermediate 3-(beta-hydroxyethyl sulfonyl) aniline
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Paragraph 0041-0044; 0058-0061; 0075-0078; 0092-0095; 0109, (2020/04/17)
The invention discloses a preparation method of dye intermediate 3-(beta-hydroxyethyl sulfonyl) aniline. The preparation method comprises the following steps: carrying out chlorosulfonation reaction on nitrobenzene and chlorosulfonic acid to obtain m-nitrobenzenesulfonyl chloride; reducing m-nitrobenzenesulfonyl chloride by using sodium pyrosulfite, and regulating the pH value of a reaction solution to 7.4-7.7 in the reaction process; adding sodium chloride after the reaction is finished, and salting out to obtain a reduction product; wherein the molar ratio of sodium pyrosulfite to m-nitrobenzenesulfonyl chloride to sodium chloride is (0.68-0.685): 1: (0.54-0.58); adding ethylene oxide into the reduction product, controlling the PH value to be 7-7.5, and reacting to obtain a condensationproduct; adopting stannous chloride and a Pd/C catalyst for reducing the condensation product to obtain 3-(beta-hydroxyethyl sulfonyl) aniline, wherein the molar ratio of the condensation product to the Pd/C catalyst is (0.45-0.46): 1: 0.0012. The preparation method provided by the invention can effectively inhibit the generation of byproducts in each process link, not only can improve the productquality, but also reduce environmental pollutants, and has a green and environment-friendly effect.
Preparation method of meta-ester and meta-ester (by machine translation)
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Paragraph 0040-0043; 0058-0061; 0076-0079; 0094-0097, (2020/06/16)
The molar ratio of the reduction product, the ethylene oxide and the sodium phosphate is 7.4 - 7.7; the molar ratio of the reduction product, the ethylene oxide and the sodium phosphate ranges from 0.68 - 0.685: (0.54 - 0.58): 7 - 7.5; the molar ratio Pd / C catalyst in each process link is controlled to 1; the product quality is improved; the environmental pollutants are reduced; and the method has the advantages of environmental protection and environmental protection effects and is obtained by esterification reaction and synthesis of the intermediate ester and Pd / C at PH ranges of (0.52 - 0.63): (0.00.12) 0.0012; and the method comprises the following steps of reducing the product, reducing environmental pollutants and 0.45 - 0.46 reducing environmental pollutants by adding sodium chloride and a Pd/C catalyst to the condensation product after the reaction is complete. (by machine translation)
Preparation method of dye intermediate 3-(beta-hydroxyethyl sulfonyl)-nitrobenzene
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Page/Page column 5-9, (2020/05/14)
The invention discloses a preparation method of a dye intermediate 3-(beta-hydroxyethyl sulfonyl)-nitrobenzene. The preparation method comprises the following steps: S1, carrying out chlorosulfonationreaction on nitrobenzene and chlorosulfonic acid to obtain m-nitrobenzenesulfonyl chloride; S2, reducing the m-nitrobenzenesulfonyl chloride by using sodium pyrosulfite, and adjusting the pH value ofthe reaction solution to 7.4-7.7 in the reaction process; adding sodium chloride after the reaction is finished, and salting out to obtain a reduction product, wherein the molar ratio of the sodium pyrosulfite to the m-nitrobenzenesulfonyl chloride to the sodium chloride is (0.68-0.685) : 1 : (0.54-0.58); and S3, adding ethylene oxide and sodium phosphate into the reduction product, controlling the pH value to be 7-7.5, and reacting to obtain 3-(beta-hydroxyethyl sulfonyl)-nitrobenzene, wherein the molar ratio of the reduction product to the ethylene oxide to the sodium phosphate is 1: (0.52-0.63): 0.00.12. The preparatio method effectively inhibits the generation of byproducts in each process link, not only improves the product quality, but also reduces environmental pollutants and has agreen and environment-friendly effect.
Preparation method for symmetric diaryl disulfide
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Paragraph 0053; 0054; 0055; 0056, (2019/04/17)
The invention discloses a preparation method for symmetric diaryl disulfide. The preparation method comprises the following steps: using aromatic hydrocarbon as shown in a general formula (I) as a rawmaterial and reacting with chlorosulfonic acid to generate aryl chlorosulfonic acid, and reacting with sulfoxide chloride to synthesize aryl sulfonyl chloride as shown in a general formula (II); andpreparing the symmetric diaryl disulfide as shown in a general formula (III) under the action of a reducing agent through a reduction reaction by the aryl sulfonyl chloride as shown in the general formula (II). The disclosed preparation method for the symmetric diaryl disulfide has many advantages of low toxicity of the reaction raw material, short reaction time, cheap reagents and easy acquisition, convenient separation and purification and the like, and has very high application value and industrial production value.
7-substituted-4-aryl coumarins compound, and preparation method and application thereof
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Paragraph 0092; 0093, (2017/08/02)
The invention discloses a 7-substituted-4-aryl coumarins compound, and a preparation method and an application thereof and belongs to the technical field of antitumor drugs. The 7-substituted-4-aryl coumarins compound is acquired in the manner of modifying and remolding 4 and 7 loci of the coumarins. The structural formula is shown in the specification. A pharmacological experiment proves that such a compound has an excellent antitumor activity, can be used for preparing the antitumor drugs, is capable of supplying a new selection for the development and application of the antitumor drugs and further can be applied to the design and optimization of the antitumor drugs. The preparation method of the compound has the advantages of easily acquired raw materials, mild reaction condition, easily realized synthesis method, simple reaction process and operation, low-cost reagents and higher yield.
Janus head type lone pair-π-lone pair and S?F?S interactions in retaining hexafluorobenzene
Mehrotra, Sonam,Angamuthu, Raja
, p. 4438 - 4444 (2016/07/06)
A series of eight tris-arylthiotriazines were synthesized to study the lone pair-π interaction between the triazine ring centroid of these molecules and halogenated solvents. All the eight compounds were characterized using 1H and 13C NMR spectroscopy and single crystal X-ray diffraction techniques. All these compounds show interesting structural properties in the solid state. Unprecedented Janus head type lp?π?lp and S?F?S interactions were observed between one of the tris-arylthiotriazines and hexafluorobenzene.
