Synthesis and acetylcholinesterase/butyrylcholinesterase inhibition activity of new tacrine-like analogues.
The synthesis and preliminary results for acetylcholinesterase and butyrylcholinesterase inhibition activity of a series of pyrano[2,3-b]quinolines (2, 3) and benzonaphthyridines (5, 6) derivatives are described. These molecules are tacrine-like analogues which have been prepared from readily available polyfunctionalized ethyl [6-amino-5-cyano-4H-pyrans and 6-amino-5-cyanopyridines]-3-carboxylates via Friedlander condensation with selected ketones. These compounds showed moderate acetylcholinesterase inhibition activity, the more potent (2e, 5b) being 6 times less active than tacrine. The butyrylcholinesterase activity of some of these molecules is also discussed.
Marco
J L
JL
Laboratorio de Radicales Libres (CSIC), Madrid, Spain. iqmc21@pinar1.csic.es
de los Ríos
C
C
Carreiras
M C
MC
Baños
J E
JE
Badía
A
A
Vivas
N M
NM
D000110:Acetylcholinesterase / Q000378:metabolism; D000544:Alzheimer Disease / Q000188:drug therapy; D002091:Butyrylcholinesterase; D002800:Cholinesterase Inhibitors / Q000138:chemical synthesis* / Q000494:pharmacology; D002802:Cholinesterases / Q000378:metabolism; D006801:Humans; D020128:Inhibitory Concentration 50; D007700:Kinetics; D009287:Naphthyridines / Q000138:chemical synthesis / Q000494:pharmacology; D011804:Quinolines / Q000138:chemical synthesis / Q000494:pharmacology; D013329:Structure-Activity Relationship; D013619:Tacrine / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000494:pharmacology
D002800:Cholinesterase Inhibitors; D009287:Naphthyridines; D011804:Quinolines; D013619:Tacrine; D000110:Acetylcholinesterase; D002091:Butyrylcholinesterase; D002802:Cholinesterases