Rapid novel divergent synthesis and muscarinic agonist profile of all four optical isomers of N,N,N-trimethyl(6-methyl-1,4-dioxan-2-yl)methanaminium iodide.
Two stereoselective parallel divergent four-step procedures to obtain all four enantiomeric forms of N,N,N-trimethyl(6-methyl-1,4-dioxan-2-yl)methanaminium iodide were developed. Enantiomeric purity was determined by quantitative (1)H NMR spectroscopy in the presence of the chiral shift reagent (+)-MTPA. The biological profile of the obtained compounds was evaluated at all muscarinic receptor subtypes by binding and functional assays.
Piergentili
Alessandro
A
Dipartimento di Scienze Chimiche, Università di Camerino, Via S. Agostino, 1, 62032 Camerino, Italy. alessandro.piergentili@unicam.it
Quaglia
Wilma
W
Giannella
Mario
M
Del Bello
Fabio
F
Buccioni
Michela
M
Nesi
Marta
M
Matucci
Rosanna
R
D000818:Animals; D016466:CHO Cells; D006224:Cricetinae; D003412:Cricetulus; D004146:Dioxanes / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D006801:Humans; D009682:Magnetic Resonance Spectroscopy; D018721:Muscarinic Agonists / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D011817:Rabbits; D013237:Stereoisomerism; D013329:Structure-Activity Relationship
D004146:Dioxanes; D018721:Muscarinic Agonists; C528979:N,N,N-trimethyl(6-methyl-1,4-dioxan-2-yl)methanaminium iodide