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

Alessandro Piergentili; Wilma Quaglia; Mario Giannella; Fabio Del Bello; Michela Buccioni; Marta Nesi; Rosanna Matucci

doi:10.1016/j.bmcl.2007.11.073

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

Bioorg Med Chem Lett. 2008 Jan 15;18(2):614-8. doi: 10.1016/j.bmcl.2007.11.073. Epub 2007 Nov 28.

Authors

Alessandro Piergentili¹, Wilma Quaglia, Mario Giannella, Fabio Del Bello, Michela Buccioni, Marta Nesi, Rosanna Matucci

Affiliation

¹ Dipartimento di Scienze Chimiche, Università di Camerino, Via S. Agostino, 1, 62032 Camerino, Italy. [email protected]

PMID: 18077164
DOI: 10.1016/j.bmcl.2007.11.073

Abstract

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.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Animals
CHO Cells
Cricetinae
Cricetulus
Dioxanes / chemical synthesis
Dioxanes / chemistry
Dioxanes / pharmacology*
Humans
Magnetic Resonance Spectroscopy
Muscarinic Agonists / chemical synthesis*
Muscarinic Agonists / chemistry
Muscarinic Agonists / pharmacology*
Rabbits
Stereoisomerism
Structure-Activity Relationship

Substances

Dioxanes
Muscarinic Agonists
N,N,N-trimethyl(6-methyl-1,4-dioxan-2-yl)methanaminium iodide