title: Two enantiomerically pure cyclic arenesulfonamide hydrochloride salts.
abstract: The crystal structures of N-[(1R)-1-(1-naphthyl)ethyl]-3,4-dihydro-2H-1,2-benzothiazin-4-aminium 1,1-dioxide chloride, C(20)H(21)N(2)O(2)S(+).Cl(-), (I), a six-membered cyclic sulfonamide, and (1R)-N-[(5,5-dioxo-6,7-dihydrodibenzo[d,f][1,2]thiazepin-7-yl)methyl]-1-(1-naphthyl)ethanaminium chloride, C(26)H(25)N(2)O(2)S(+).Cl(-), (II), a seven-membered cyclic sulfonamide, both representative of a novel family of agonists of the extracellular calcium sensing receptor (CaSR) of possible clinical importance, are reported. The known chirality of the naphthylethylamine precursor has enabled assignment of the absolute configuration of both compounds, which is crucial for the receptor recognition. The crystal structures, though different, reveal for these agonists a notable absence of intramolecular pi-pi stacking between their respective aromatic groups. This suggests a common structural feature that allows CaSR agonists to be distinguished from antagonists, since in the latter, such interactions have been shown to be important. The connectivities between molecules in the crystal structures are also different, but both involve hydrogen bonding mediated by chloride ions as a common dominant feature.
authors.affiliation: Institut de Chimie des Substances Naturelles, UPR 2301, Centre National de la Recherche Scientifique, Bâtiment 27, 1 Avenue de la Terrasse, F-91198 Gif-sur-Yvette, France.
authors.forename: Lionel
authors.initials: L
authors.lastname: Kiefer
authors.forename: Philippe
authors.initials: P
authors.lastname: Dauban
authors.forename: Robert H
authors.initials: RH
authors.lastname: Dodd
authors.forename: Pascal
authors.initials: P
authors.lastname: Retailleau
mesh_terms: D018360:Crystallography, X-Ray; D003499:Cyclic S-Oxides / Q000737:chemistry*; D003987:Dibenzothiazepines / Q000737:chemistry*; D006860:Hydrogen Bonding; D008958:Models, Molecular; D012492:Salts / Q000737:chemistry; D013237:Stereoisomerism; D013449:Sulfonamides / Q000737:chemistry*; D013843:Thiazines / Q000737:chemistry*
chemical_list: D003499:Cyclic S-Oxides; D003987:Dibenzothiazepines; C539854:N-((5,5-dioxo-6,7-dihydrodibenzo(d,f)(1,2)thiazepin-7-yl)methyl)-1-(1-naphthyl)ethanamine; C539853:N-(1-(1-naphthyl)ethyl)-3,4-dihydro-2H-1,2-benzothiazin-4-amine 1,1-dioxide; D012492:Salts; D013449:Sulfonamides; D013843:Thiazines