Methylation of the carbon atom C1 of compound 1, a potent and not selective muscarinic antagonist, was carried out. The resulting diastereomers were separated and the corresponding racemate further resolved to give four enantiomers, which were tested both as hydrogen oxalate and methiodide salts. The pharmacological results obtained at M-1, M-2 and M-3 muscarinic receptor subtypes, show that methylation at C1, depending on the stereochemistry, increases antagonist potency, having thus the same effect of nitrogen quaternization. These results may well lead to the development of new potent antimuscarinic drugs lacking a cationic head. (C) 2001 Elsevier Science Ltd. All rights reserved.

Synthesis, absolute configuration and antimuscarinic activity of the enantiomers of [1-(2,2-diphenyl-[1,3]dioxolan-4-yl)-ethyl]dimethyl-amine / U., Gulini; P., Angeli; G., Marucci; M., Buccioni; D., Giardina; Antolini, Luciano; Franchini, Silvia; Sorbi, Claudia; Brasili, Livio. - In: BIOORGANIC & MEDICINAL CHEMISTRY LETTERS. - ISSN 0960-894X. - STAMPA. - 11:2(2001), pp. 247-250. [10.1016/S0960-894X(00)00647-8]

Synthesis, absolute configuration and antimuscarinic activity of the enantiomers of [1-(2,2-diphenyl-[1,3]dioxolan-4-yl)-ethyl]dimethyl-amine

ANTOLINI, Luciano;FRANCHINI, Silvia;SORBI, Claudia;BRASILI, Livio
2001

Abstract

Methylation of the carbon atom C1 of compound 1, a potent and not selective muscarinic antagonist, was carried out. The resulting diastereomers were separated and the corresponding racemate further resolved to give four enantiomers, which were tested both as hydrogen oxalate and methiodide salts. The pharmacological results obtained at M-1, M-2 and M-3 muscarinic receptor subtypes, show that methylation at C1, depending on the stereochemistry, increases antagonist potency, having thus the same effect of nitrogen quaternization. These results may well lead to the development of new potent antimuscarinic drugs lacking a cationic head. (C) 2001 Elsevier Science Ltd. All rights reserved.
2001
11
2
247
250
Synthesis, absolute configuration and antimuscarinic activity of the enantiomers of [1-(2,2-diphenyl-[1,3]dioxolan-4-yl)-ethyl]dimethyl-amine / U., Gulini; P., Angeli; G., Marucci; M., Buccioni; D., Giardina; Antolini, Luciano; Franchini, Silvia; Sorbi, Claudia; Brasili, Livio. - In: BIOORGANIC & MEDICINAL CHEMISTRY LETTERS. - ISSN 0960-894X. - STAMPA. - 11:2(2001), pp. 247-250. [10.1016/S0960-894X(00)00647-8]
U., Gulini; P., Angeli; G., Marucci; M., Buccioni; D., Giardina; Antolini, Luciano; Franchini, Silvia; Sorbi, Claudia; Brasili, Livio
File in questo prodotto:
Non ci sono file associati a questo prodotto.
Pubblicazioni consigliate

Licenza Creative Commons
I metadati presenti in IRIS UNIMORE sono rilasciati con licenza Creative Commons CC0 1.0 Universal, mentre i file delle pubblicazioni sono rilasciati con licenza Attribuzione 4.0 Internazionale (CC BY 4.0), salvo diversa indicazione.
In caso di violazione di copyright, contattare Supporto Iris

Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11380/306286
Citazioni
  • ???jsp.display-item.citation.pmc??? 0
  • Scopus 2
  • ???jsp.display-item.citation.isi??? 0
social impact