Abstract:
A series of α-and β-isomers of 3-methyl-3-azabicyclo-3,3,1 nonan-9-yl substituted carboxylic esters were synthesized. The starting material 3methyl-3-azabicyclo 3,3,1 nonan-9-one was prepared from cyclohexanone, methylamine and formaldehyde by Mannich reaction. The ketone was reduced and separated into 9
α and 9
β alcohols, and the isomeric alcohols were esterified separately with various methyl carboxylates to give the corresponding esters Ⅲ
1~10. The stereochemistry of these esters were identified by means of
1HNMR.Preliminary pharmacological results showed that, except compounds Ⅲ
9 and Ⅲ
10 all compounds exhibited potent central anticholinergic activities, six of them were equal to or more potent than atropine. The
α and
β isomers of each pair were close in their anticholinergic activity in 9
α,
βisomers of 3-methyl-3-azabicyclo 3,3,1 nonanyl esters.