41345-36-2Relevant academic research and scientific papers
Preparation of sodium sulfonates using by copper as catalyst
Bai, Ruijiao,Zhang, Richeng,Qi, Haofei,Yan, Xilong,Chen, Ligong
, p. 7226 - 7228 (2015/04/22)
The sodium alkyl sulfonates were prepared by Strecker reaction. The synthesis of sodium chloroethyl sulfonate from dichloroethane and sodium sulfite with different catalysts, it was found that copper was an efficient catalyst with a yield (81%). The reaction conditions were also optimized to make the route more competitive and suitable for large-scale industrial production. Besides, some more sulfonates were also obtained with copper as catalyst via Strecker reaction.
Access to a wide range of sultams by cyclodialkylation of α-substituted methanesulfonanilides
Rassadin, Valentin A.,Grosheva, Daria S.,Arefeva, Irina A.,Tomashevskiy, Aleksandr A.,Sokolov, Victor V.,De Meijere, Armin
supporting information, p. 5028 - 5037,10 (2020/08/24)
A wide range of five- and six-membered sultams bearing an α-ethoxycarbonyl-α-methyl substituent or an α-aryl group (17 examples) were synthesized by the cyclodialkylation of α-substituted methanesulfonanilides with α,ω-dihaloalkanes in the presence of K2CO3 or under phase-transfer catalysis (PTC) conditions. Upon treatment with K2CO3 in N,N-dimethylformamide (DMF) or NaH in dimethyl sulfoxide (DMSO), N-(2,3-dibromopropyl)-α- toluenesulfonanilides furnished different 1,3-diaryl-2-thia-3-azabicyclo[3.1.0] hexane 2,2-dioxides in good to excellent yields (51-88 %, 16 examples). The 4-methoxyphenyl (PMP) group was easily removed from the sultam nitrogen atom by treatment of the corresponding bicyclic sultams with cerium(IV) ammonium nitrate in acetonitrile (71-84 % yield, 6 examples). The intermolecular cyclodialkylation of α-substituted methanesulfonamides constitutes a simple and efficient route to five- and six-membered sultams with α-ethoxycarbonyl-α-methyl or α-aryl substitution. The intramolecular cyclodialkylation of N-(2,3-dibromopropyl)-α- toluenesulfanilides readily leads to bicyclic sultams bearing a cyclopropane ring. Copyright
N-1H-Benzimidazol-5-ylbenzenesulfonamide derivatives as potent hPXR agonists
Benod, Cindy,Subra, Guy,Nahoum, Virginie,Mallavialle, Aude,Guichou, Jean-Francois,Milhau, Julien,Robles, Samuel,Bourguet, William,Pascussi, Jean-Marc,Balaguer, Patrick,Chavanieu, Alain
, p. 3537 - 3549 (2008/12/20)
The Human Pregnane X Receptor (hPXR) is a nuclear receptor that regulates the expression of phase I and phase II drug-metabolizing enzymes, as well as that of drug transporters. Because this receptor plays a critical role in protecting tissues from potentially toxic endo- and xenobiotics, highly active agonists could represent novel therapeutic tools in treating several human diseases. Using an in vitro screening reporter system that allow to characterize hPXR activators and a first step of chemical modifications of an original agonist ligand (C2BA-4, 1-(2-chlorophenyl)-N-[1-(1-phenylethyl)-1H-benzimidazol-5-yl]methanesulf onamide), we identified compounds with a N-1H-benzimidazol-5-ylbenzenesulfonamide scaffold as a potent family of hPXR agonists. Further chemical modifications allowed us to identify enhanced activators, notably N-(1-benzyl-1H-benzimidazol-5-yl)-2,3,4,5,6-pentamethylbenzenesulfonamid e (6n) with an EC50 value in the subnanomolar range. Accordingly to their potent EC50, these compounds induced an efficient protection of hPXR against proteolytic digestion by trypsin even at very low ligand concentrations and were able to induce the expression of the main target genes of hPXR, CYP3A4 and CYP2B6, in primary cultures of human hepatocytes.
