178693-27-1Relevant articles and documents
Systematic variation of the benzenesulfonamide part of the GluN2A selective NMDA receptor antagonist TCN-201
Müller, Sebastian L.,Schreiber, Julian A.,Schepmann, Dirk,Strutz-Seebohm, Nathalie,Seebohm, Guiscard,Wünsch, Bernhard
supporting information, p. 124 - 134 (2017/02/23)
GluN2A subunit containing N-methyl-D-aspartate receptors (NMDARs) are highly involved in various physiological processes in the central nervous system, but also in some diseases, such as anxiety, depression and schizophrenia. However, the role of GluN2A subunit containing NMDARs in pathological processes is not exactly elucidated. In order to obtain potent and selective inhibitors of GluN2A subunit containing NMDARs, the selective negative allosteric modulator 2 was systematically modified at the benzenesulfonamide part. The activity of the test compounds was recorded in two electrode voltage clamp experiments using Xenopus laevis oocytes expressing exclusively NMDARs with GluN1a and GluN2A subunits. It was found that halogen atoms in 3-position of the benzenesulfonamide part result in high GluN2A antagonistic activity. With an IC50 value of 204?nM the 3-bromo derivative 5i (N-{4-[(2-benzoylhydrazino)carbonyl]benzyl}-3-bromobenzenesulfonamide) has 2.5-fold higher antagonistic activity than the lead compound 2 and represents our new lead compound.
Solvent hydrogen bonding and structural effects on nucleophilic substitution reactions. Part-7: Reaction of benzenesulphonyl chloride with substituted benzylamines in acetonitrile/dimethylsulfoxide mixtures
Thirumoorthi,Elango
body text, p. 797 - 802 (2011/04/22)
Substitution reactions of eleven para- and meta-substituted benzylamines with benzenesulphonyl chloride in different mole fractions of dimethylsulfoxide (DMSO) in acetonitrile (AcN) have been investigated conductometrically. The second order rate constants found to increase with an increase in the mole fraction of DMSO up to 0.5 mole fraction and beyond that it remained nearly constant. Multiple correlation analysis of the rate data via Kamlet-Taft's solvatochromic parameters revealed that the solvent H-bonding and dipolarity/polarizability plays a dominant role in governing the reactivity and also solvent-solvent interaction influenced the preferential solvation and consequently the rate of the reaction. A curved Hammett plot was obtained and a mechanism was proposed to account for this nonlinear behaviour observed.
Novel histone deacetylase inhibitors: N-hydroxycarboxamides possessing a terminal bicyclic aryl group
Uesato, Shinichi,Kitagawa, Manabu,Nagaoka, Yasuo,Maeda, Taishi,Kuwajima, Hiroshi,Yamori, Takao
, p. 1347 - 1349 (2007/10/03)
Utilizing tranexamic acid as a starting material, a series of N-hydroxycarboxamides were synthesized in order to seek new histone deacetylase (HDAC) inhibitors. Further structure optimization involving the replacement of the 1,4-cyclohexylene group with t