29083-16-7Relevant articles and documents
Synthesis of 3,4-dihydro-2H-1,2-benzothiazine-3-carboxylic acid 1,1-dioxides and their evaluation as ligands for NMDA receptor glycine binding site
Bluke, Zanda,Paass, Einars,Sladek, Meik,Abel, Ulrich,Kauss, Valerjans
, p. 664 - 673 (2016)
A series of 2-substituted 3,4-dihydro-2H-1,2-benzothiazine-3-carboxylic acid 1,1-dioxides were synthesized and evaluated for their affinity to the glycine binding site of the N-methyl-d-aspartate (NMDA) receptor. The binding affinity was determined by the displacement of radioligand [3H]MDL-105,519 from rat cortical membrane preparations. The most attractive structures in the search for prospective NMDA receptor ligands were identified to be 2-arylcarbonylmethyl substituted 3,4-dihydro-2H-1,2-benzothiazine-3-carboxylic acid 1,1-dioxides. It has been demonstrated for the first time that the replacement of NH group in the ligand by sp3 CH2 is tolerated. This finding may pave the way for previously unexplored approaches for designing new ligands of the NMDA receptor.
Oxidative cyclization of N-alkyl-o-methyl-arenesulfonamides to biologically important saccharin derivatives
Xu, Liang,Shu, Hong,Liu, Ying,Zhang, Suhong,Trudell, Mark L.
, p. 7902 - 7910 (2007/10/03)
Various biologically important saccharin skeletons and their N-alkyl derivatives have been efficiently prepared by chromium(VI) oxide catalyzed H5IO6 oxidation of N-alkyl-o-methyl-arenesulfonamides in acetonitrile. N-tert-Butyl saccharin skeletons were easily prepared by H5IO6-CrO3 oxidation of N-tert-butyl-o-methyl arenesulfonamides in the presence of acetic anhydride. The method that furnished the novel fluoro and trifluoromethyl substituted saccharin skeletons is characterized by two steps, a simple work-up procedure, a single purification and good overall yields from substituted toluene derivatives.
The Reaction of Saccharin Derivatives with N,N-Diethylprop-1-ynamine: Formation of Cyclobutenyl Saccharinates and of a Spiro-oxete
Abramovitch, Rudolph A.,Ooi, Gino H. C.,Sun, Han-Li,Pierrot, Marcel,Baldy, Andre,Estienne, Jacques
, p. 1583 - 1584 (2007/10/02)
Saccharin and two equivalents of N,N-diethylprop-1-ynamine give a cyclobutenyl saccharinate (4) which, on bromination, gives the N-(cyclobutenyl cation)saccharin derivative (8), whose structure was established by X-ray crystallography ; N-methylsaccharin reacts with one equivalent of ynamine to yield the spiro-oxete (9): this represents the second isolation of such a stable oxete from reaction of an ynamine with a carbonyl group.