736153-76-7Relevant articles and documents
Preliminary synthetic studies of methyllycaconitine, a potent nicotinic acetylcholine receptor antagonist: Rapid syntheses of AE-Bicyclic analogues
Coates, Philippa A.,Blagbrough, Ian S.,Rowan, Michael G.,Pearson, David P. J.,Lewis, Terence,Potter, Barry V. L.
, p. 210 - 213 (1996)
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 h
Synthesis of simple analogues of methyllycaconitine - An efficient method for the preparation of the N-substituted anthranilate pharmacophore
Barker, David,Brimble, Margaret A.,McLeod, Malcolm D.
, p. 5953 - 5963 (2007/10/03)
The synthesis of several A and AE ring analogues of the alkaloid methyllycaconitine is reported. The key 2-(2″-methylsuccinimido)benzoate ester pharmacophore is introduced using an efficient two step procedure. Esterification of the alcohol precursors with N-(trifluoroacetyl)anthranilic acid under Steglich conditions followed by sodium borohydride mediated cleavage of the trifluoroacetyl group affords the anthranilate esters. Subsequent fusion with methylsuccinic anhydride affords the N-substituted anthranilate derivatives containing the key pharmacophore present in a range of commonly occurring Delphinium and Aconitum alkaloids.
