The synthesis and preliminary results for acetylcholinesteraseand butyrylcholinesterase inhibition activation 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-cyano-pyridines]-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. Copyright © 2001 Elsevier Science Ltd.