Completing a long-lasting research on 1,3-oxathiolane muscarinic ligands, we have synthesized a set of isomeric 1-methyl-2-(2,2-alkylaryl-1,3-oxathiolan-5-yl)pyrrolidine 3-sulfoxide derivatives, containing three or four stereogenic centers. In general the compounds are very potent antagonists even if, unlike the corresponding agonists, they show modest subtype selectivity.
Muscarinic antagonists with multiple stereocenters: synthesis, affinity profile and functional activity of isomeric 1-methyl-2-(2,2-alkylaryl-1,3-oxathiolan-5-yl)pyrrolidine sulfoxide derivatives / Dei, Silvia; Bellucci, Cristina; Buccioni, M.; Ferraroni, Marta; Guandalini, Luca; Manetti, Dina; Marucci, G.; Matucci, Rosanna; Nesi, Marta; Romanelli, MARIA NOVELLA; Scapecchi, Serena; Teodori, Elisabetta. - In: BIOORGANIC & MEDICINAL CHEMISTRY. - ISSN 0968-0896. - STAMPA. - 16:(2008), pp. 5490-5500. [10.1016/j.bmc.2008.04.013]
Muscarinic antagonists with multiple stereocenters: synthesis, affinity profile and functional activity of isomeric 1-methyl-2-(2,2-alkylaryl-1,3-oxathiolan-5-yl)pyrrolidine sulfoxide derivatives
DEI, SILVIA;BELLUCCI, CRISTINA;FERRARONI, MARTA;GUANDALINI, LUCA;MANETTI, DINA;MATUCCI, ROSANNA;NESI, MARTA;ROMANELLI, MARIA NOVELLA;SCAPECCHI, SERENA;TEODORI, ELISABETTA
2008
Abstract
Completing a long-lasting research on 1,3-oxathiolane muscarinic ligands, we have synthesized a set of isomeric 1-methyl-2-(2,2-alkylaryl-1,3-oxathiolan-5-yl)pyrrolidine 3-sulfoxide derivatives, containing three or four stereogenic centers. In general the compounds are very potent antagonists even if, unlike the corresponding agonists, they show modest subtype selectivity.
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