Design and synthesis of cyclic sulfonamides and sulfamates as new calcium sensing receptor agonists.

Lionel Kiefer (1) , Tatiana Gorojankina (2, 3) , Philippe Dauban (1) , Hélène Faure (2, 3) , Martial Ruat (2, 3) , Robert H. Dodd (1)

1 ICSN - Institut de Chimie des Substances Naturelles
2 INAF - Institut de Neurobiologie Alfred Fessard
3 N&eD - Neurobiologie et Développement

The design, synthesis and calcimimetic properties of various cyclic sulfonamides and sulfamates are described. The latter were prepared from the corresponding o-alkenylarenesulfonamides via copper- or rhodium-catalyzed intramolecular aziridination. The size of the cyclic sulfonamide rings as well as the position of the crucial (R)-naphthylethylamine substituent significantly affected calcimimetic activity. The most active compounds were the six- and seven-membered sulfonamides 30a and 31a and sulfamate 34a.

Domaines: Neurosciences [q-bio.NC]; Chimie organique

Lionel Kiefer, Tatiana Gorojankina, Philippe Dauban, Hélène Faure, Martial Ruat, et al.. Design and synthesis of cyclic sulfonamides and sulfamates as new calcium sensing receptor agonists.. Bioorganic and Medicinal Chemistry Letters, 2010, 20 (24), pp.7483-7487. ⟨10.1016/j.bmcl.2010.10.006⟩. ⟨hal-00537890⟩