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Synthesis of simple analogues of methyllycaconitine—an efficient method for the preparation of the N-substituted anthranilate pharmacophore |
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| Authors: | David Barker Malcolm D McLeod |
| Affiliation: | a School of Chemistry, F11, University of Sydney, Camperdown, NSW 2006, Australia b Department of Chemistry, University of Auckland, Private Bag 92019, 23 Symonds St., Auckland, New Zealand |
| Abstract: | 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. |
| Keywords: | Methyllycaconitine Anthranilate esters Nicotinic acetylcholine receptors Alkaloids |
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