184592-41-4Relevant academic research and scientific papers
Sulfonamide Synthesis through Electrochemical Oxidative Coupling of Amines and Thiols
Laudadio, Gabriele,Barmpoutsis, Efstathios,Schotten, Christiane,Struik, Lisa,Govaerts, Sebastian,Browne, Duncan L.,No?l, Timothy
supporting information, (2019/04/16)
Sulfonamides are key motifs in pharmaceuticals and agrochemicals, spurring the continuous development of novel and efficient synthetic methods to access these functional groups. Herein, we report an environmentally benign electrochemical method which enables the oxidative coupling between thiols and amines, two readily available and inexpensive commodity chemicals. The transformation is completely driven by electricity, does not require any sacrificial reagent or additional catalysts and can be carried out in only 5 min. Hydrogen is formed as a benign byproduct at the counter electrode. Owing to the mild reaction conditions, the reaction displays a broad substrate scope and functional group compatibility.
Sulfonamide Synthesis through Electrochemical Oxidative Coupling of Amines and Thiols
Laudadio, Gabriele,Barmpoutsis, Efstathios,Schotten, Christiane,Struik, Lisa,Govaerts, Sebastian,Browne, Duncan L.,No?l, Timothy
supporting information, p. 5664 - 5668 (2019/04/17)
Sulfonamides are key motifs in pharmaceuticals and agrochemicals, spurring the continuous development of novel and efficient synthetic methods to access these functional groups. Herein, we report an environmentally benign electrochemical method which enables the oxidative coupling between thiols and amines, two readily available and inexpensive commodity chemicals. The transformation is completely driven by electricity, does not require any sacrificial reagent or additional catalysts and can be carried out in only 5 min. Hydrogen is formed as a benign byproduct at the counter electrode. Owing to the mild reaction conditions, the reaction displays a broad substrate scope and functional group compatibility.
IMIDAZOLIDINONE DERIVATIVES
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Page/Page column 18, (2008/12/07)
The invention is concerned with novel imidazolidinone derivatives of formula (I): wherein R1 to R11 and X are as defined in the description and in the claims, as well as physiologically acceptable salts thereof. These compounds bind
Metal oxide in aqueous organic solution promoted chemoselective N-sulfonylation of hydrophilic amino alcohols
Kang, Hak Hee,Rho, Ho Sik,Kim, Duck Hee,Oh, Seong-Geun
, p. 7225 - 7227 (2007/10/03)
The reaction of hydrophilic amino alcohols with sulfonyl chlorides in the presence of metal oxide (MgO, CuO, Ag2O) in aqueous organic solution cleanly provided alkanolsulfonamide. Advantages of this method were mild, neutral reaction conditions
Desulfonylation of amides using tributyltin hydride, samarium diiodide or zinc/titanium tetrachloride. A comparison of methods
Knowles, Haydn S.,Parsons, Andrew F.,Pettifer, Robert M.,Rickling, Stéphane
, p. 979 - 988 (2007/10/03)
Deprotection of N-sulfonylated amides can be achieved by reaction with Bu3SnH, SmI2 or TiCl4/Zn. All three methods gave good yields (typically >60%) when using N-benzoyl or related amides while the corresponding N~acetyl derivatives proved to be inert to deprotection under the same reaction conditions. The mechanistic implications of this are discussed. (C) 2000 Elsevier Science Ltd.
Synthesis and protein kinase C inhibitory activities of acyclic balanol analogs that are highly selective for protein kinase C over protein kinase A
Defauw, Jean M.,Murphy, Marcia M.,Jagdmann Jr., G. Erik,Hu, Hong,Lampe, John W.,Hollinshead, Sean P.,Mitchell, Thomas J.,Crane, Heidi M.,Heerding, Julia M.,Mendoza, José S.,Davis, Jefferson E.,Darges, James W.,Hubbard, Frederick R.,Hall, Steven E.
, p. 5215 - 5227 (2007/10/03)
A series of balanol analogs in which the perhydroazepine ring and the p- hydroxybenzamide moiety were combined into an acyclic linked unit have been prepared and evaluated for their inhibitory properties against the serine/threonine kinase PKC. Several low-micromolar to lownanomolar inhibitors of the α, β'(I), β(II), γ, δ, ε, and η PKC isozymes were prepared. In general, these acyclic balanol analogs were found to be highly selective for PKC over the serine/threonine kinase PKA. The type and number of atoms linking the benzophenone ester to the p-hydroxyphenyl group necessary for optimal PKC inhibition were investigated. The most potent compounds contained a three-carbon linker in which the carboxamide moiety of balanol had been replaced by a methylene group. The effect of placing substituents on the three-carbon chain was also investigated. The preferred compounds contained either a 2-benzene-sulfonamido (6b) or a 1-methyl (21b) substituent. The preferred compounds 6b and 21b were tested against a panel of serine/threonine kinases and found to be highly selective for PKC. The more active enantiomer of 6b, (S)-12b, was 3-10-fold more active than the R- enantiomer against the PKC isozymes. The effect of making the analogs more rigid by making the three-carbon chain part of a five-membered ring, but with retention of the methylene replacement for the carboxamide moiety, led to potent PKC inhibitors including anti-substituted pyrrolidine analog 35b and the most potent PKC inhibitor in the series, anti-substituted cyclopentane analog 29b. The anti cyclopentane analog 29b was a low-micromolar inhibitor of the PMA-induced superoxide burst in neutrophils, and its carboxylic ester was a high-nanomolar inhibitor of neutrophils. Finally esterification of 21b, (S)-12b, and 35b turned these potent PKC inhibitors into low-micromolar inhibitors of neutrophils.
