Synthesis and acetylcholinesterase inhibition of 5-desamino huperzine A derivatives.
(E)- and (Z)-5-Desamino huperzine A derivatives have been synthesized using a new synthetic strategy towards the huperzine A skeleton. These derivatives showed AChE inhibition constants in the low micromolar range and thus display better activity than all previously synthesized C5 derivatives.
Högenauer
K
K
Institut für Organische Chemie, Universität Wien, Währingerstrasse 38, A-1090 Wien, Austria.
Baumann
K
K
Enz
A
A
Mulzer
J
J
D000110:Acetylcholinesterase / Q000378:metabolism; D000818:Animals; D001952:Bridged-Ring Compounds / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D002800:Cholinesterase Inhibitors / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D006575:Heterocyclic Compounds, 3-Ring / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D051381:Rats; D017207:Rats, Sprague-Dawley
C439167:5-desamino huperzine A; D001952:Bridged-Ring Compounds; D002800:Cholinesterase Inhibitors; D006575:Heterocyclic Compounds, 3-Ring; D000110:Acetylcholinesterase