- Cobalt-Catalyzed 1,4-Aryl Migration/Desulfonylation Cascade: Synthesis of α-Aryl Amides
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A cobalt-catalyzed 1,4-aryl migration/disulfonylation cascade applied to α-bromo N-sulfonyl amides was developed. The reaction was highly chemoselective, allowing the preparation of α-aryl amides possessing a variety of functional groups. The method was used as the key step to synthesize an alkaloid, (±)-deoxyeseroline. Mechanistic investigations suggest a radical process.
- Gillaizeau-Simonian, Nicolas,Barde, Etienne,Guérinot, Amandine,Cossy, Janine
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supporting information
p. 4004 - 4008
(2021/02/11)
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- Method for catalytic synthesis of N-benzyl benzene sulfonamide compounds by boric acid/oxalic acid catalytic system under microwave radiation
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The invention discloses a method for catalytic synthesis of N-benzyl benzene sulfonamide compounds by a boric acid/oxalic acid catalytic system under microwave radiation. The method includes: adoptingbenzyl alcohol and derivatives thereof and benzene sulfonamide derivatives as raw materials, adopting the boric acid/oxalic acid system as a catalyst, and adopting fluorobenzene as a solvent; performing reaction in a microwave reactor under certain temperature and power conditions, performing vacuum concentration after reaction for a period of time, and subjecting a product to column chromatographic purification to realize efficient catalytic preparation of the N-benzyl benzene sulfonamide compounds. Compared with the prior art, the method has advantages of evidently higher reaction speed than that of conventional heating, mild reaction conditions, simplicity in operation, high yield, safety, low cost and environmental friendliness.
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Paragraph 0031; 0083
(2018/09/11)
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- ADENINE DERIVATIVES AS PROTEIN KINASE INHIBITORS
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The present invention relates to a compound suitable for use as a kinase inhibitor according to general formula (I) [compound (C), herein after], or the N- oxide, pharmaceutically acceptable salt, pharmaceutically acceptable solvate, or stereoisomer thereof, formula (I) wherein A, R1, R2, R3, R3', R4, R4', X, Y, Z, T are as defined in the claims. The invention further relates to an in vitro method of inhibiting protein kinase activity which comprises contacting a protein kinase with a compound of formula (I), or the N-oxide, pharmaceutically acceptable salt, pharmaceutically acceptable solvate, or stereoisomer thereof. The invention further relates to the compounds of formula (I) per se, as well as to their use as a medicament, and for use or in a method of treatment of a disease mediated by a protein kinase selected from cancer, inflammatory disorders, cardiovascular diseases, viral induced diseases, circulatory diseases, fibro-proliferative diseases and pain sensitization disorders.
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Page/Page column 129
(2017/12/14)
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- Synthesis process of sulfonamide compounds in microwave system
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The invention discloses a synthesis process of sulfonamide compounds in a microwave system. The synthesis process is realized by the following steps: by using CuCl as a catalyst and FeCl3 as an oxidant, carrying out carbon-hydrogen activating and carbon-nitrogen coupling reaction in a DMF (Dimethyl Formamide) by substituting sulfanilamide and methylbenzene through microwave heating and efficient catalysis for 10 to 60 minutes; extracting a product by using ethyl acetate; carrying out vacuum concentration; carrying out column chromatographic purification on a product to obtain the sulfonamide compounds. The synthesis process is a method for efficiently preparing the sulfonamide compounds, which is environment-friendly and is simple and convenient to operate. Compared with the prior art, the synthetic process disclosed by the invention has the advantages of remarkably-increased reaction speed compared with that under a conventional heating condition, mild reaction conditions, simple operation, high yield, safety, low cost and environmental protection.
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Paragraph 0007; 0021; 0033
(2017/08/14)
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- Active site mapping of trypsin, thrombin and matriptase-2 by sulfamoyl benzamidines
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The benzamidine moiety, a well-known arginine mimetic, has been introduced in a variety of ligands, including peptidomimetic inhibitors of trypsin-like serine proteases. According to their primary substrate specificity, the benzamidine residue interacts with the negatively charged aspartate at the bottom of the S1 pocket of such enzymes. Six series of benzamidine derivatives (1-73) were synthesized and evaluated as inhibitors of two prototype serine proteases, that is, bovine trypsin and human thrombin. As a further target, human matriptase-2, a recently discovered type II transmembrane serine protease, was investigated. Matriptase-2 represents an important regulatory protease in iron homeostasis by down-regulation of the hepcidin expression. Compounds 1-73 were designed to contain a fixed sulfamoyl benzamidine moiety as arginine mimetic and a linker-connected additional substructure, such as a tert-butyl ester, carboxylate or second benzamidine functionality. A systematic mapping approach was performed with these inhibitors to scan the active site of the three target proteases. In particular, bisbenzamidines, able to interact with both the S1 and S3/S4 binding sites, showed notable affinity. In branched bisbenzamidines 66-73 containing a third hydrophobic residue, opposite effects of the stereochemistry on trypsin and thrombin inhibition were observed.
- Dosa, Stefan,Stirnberg, Marit,Luelsdorff, Verena,Haeussler, Daniela,Maurer, Eva,Guetschow, Michael
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supporting information
p. 6489 - 6505,17
(2012/12/11)
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- Biaryl sulfonamides from O-acetyl amidoximes: 1,2,4-Oxadiazole cyclization under acidic conditions
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A series of 4-cyanobenzenesulfonamides (1a-h) was converted to the corresponding O-acetylated amidoximes (2a-h). The reaction of 1a was exemplarily investigated with respect to the formation of a byproduct, which was identified as 1,2,4-oxadiazole derivative 3a. This observation led to the development of an improved procedure for the preparation of 2a-h. Compounds 2 could be transformed to 1,2,4-oxadiazoles 3a-h in high yields and purity upon heating in acetic acid.
- Dosa, Stefan,Daniels, Joerg,Guetschow, Michael
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experimental part
p. 407 - 413
(2011/05/14)
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- SULFAMOYL BENZOIC ACID DERIVATIVES AS TRPM8 ANTAGONISTS
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The present invention relates to sulfamoyl benzoic acid derivatives of formula (I) or a pharmaceutically acceptable salt thereof, processes for their preparation, pharmaceutical compositions containing them and their use in the treatment of various disorders which are mediated via the TRPM8 receptor.
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Page/Page column 98
(2010/11/17)
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- 2-AMINO-PYRIDINE DERIVATIVES AS BETA-2 ADRENORECEPTOR AGONISTS
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The invention relates to compounds of formula (1) and to processes for the preparation of, intermediates used in the preparation of, compositions containing and the uses of, such derivatives. The compounds according to the present invention are useful in
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- Synthesis and cathodic cleavage of a set of substituted benzenesulfonamides including the corresponding tert-butyl sulfonylcarbamates: pKa of sulfonamides
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From a series of substituted benzenesulfonic acids, most of which have previously been employed for the protection of amino functions and including a few such known to facilitate cleavage by acid, benzylamides 1a-k have been derived and studied.Initially their electrochemical cleavage potentials were determined by cyclic voltammetry in order to further explore selective deprotection within this substance group.In parallel, the corresponding tert-butyl sulfonylcarbamates 2a-k have also been prepared and studied.Among the sulfonamides investigated S-N bond cleavage was found to take place over a wide range of potentials from -1.67 to -2.64 V (excluding the nitro derivative), the most acid-labile groups requiring more negative potentials, whereas this cleavage was facilitated by 0.19-0.39 V for the sulfonylcarbamates.Small scale electolyses of 2 at controlled potential with determination of the cleavage products formed were subsequently performed.For the N-benzylbenzenesulfonamides, 1, the pKas in DMSO and in some cases also in water have been determined and found to be in the range 14.0-16.4 and 10.07-11.53, respectively.
- Nyasse, Barthelemy,Grehn, Leif,Ragnarsson, Ulf,Maia, Hernani L. S.,Monteiro, Luis S.,et al.
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p. 2025 - 2032
(2007/10/02)
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