title: Preliminary synthetic studies of methyllycaconitine, a potent nicotinic acetylcholine receptor antagonist: rapid syntheses of AE-bicyclic analogues.
abstract: 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.
authors.affiliation: Department of Medicinal Chemistry, University of Bath, Claverton Down, UK.
authors.forename: P A
authors.initials: PA
authors.lastname: Coates
authors.forename: I S
authors.initials: IS
authors.lastname: Blagbrough
authors.forename: M G
authors.initials: MG
authors.lastname: Rowan
authors.forename: D P
authors.initials: DP
authors.lastname: Pearson
authors.forename: T
authors.initials: T
authors.lastname: Lewis
authors.forename: B V
authors.initials: BV
authors.lastname: Potter
mesh_terms: D000157:Aconitine / Q000031:analogs & derivatives* / Q000138:chemical synthesis; D007306:Insecticides / Q000138:chemical synthesis*; D015394:Molecular Structure
chemical_list: D007306:Insecticides; C093992:lycoctonine; C054634:methyllycaconitine; D000157:Aconitine