Preliminary synthetic studies of methyllycaconitine, a potent nicotinic acetylcholine receptor antagonist: rapid syntheses of AE-bicyclic analogues.
A series of bicyclic analogues incorporating the homocholine motif of methyllycaconitine has been prepared to test the hypothesis that this is the essential pharmacophore of this potent, selective nicotinic receptor antagonist. A double Mannich reaction has been employed to construct the 3-azabicyclo[3.3.1]-nonane ring system, containing an N-ethylpiperidine moiety. The neopentyl-like alcohol was then esterified, using isatoic anhydride under basic conditions, to afford the corresponding anthranilate.
Coates
P A
PA
Department of Medicinal Chemistry, University of Bath, Claverton Down, UK.
Blagbrough
I S
IS
Rowan
M G
MG
Pearson
D P
DP
Lewis
T
T
Potter
B V
BV
D000157:Aconitine / Q000031:analogs & derivatives* / Q000138:chemical synthesis; D007306:Insecticides / Q000138:chemical synthesis*; D015394:Molecular Structure
D007306:Insecticides; C093992:lycoctonine; C054634:methyllycaconitine; D000157:Aconitine