Synthesis of tricyclic analogs of stephaoxocanidine and their evaluation as acetylcholinesterase inhibitors

Darío A Bianchi; Guillermo Schmeda Hirschmann; Cristina Theoduloz; Andrea B J Bracca; Teodoro S Kaufman

doi:10.1016/j.bmcl.2005.04.005

Synthesis of tricyclic analogs of stephaoxocanidine and their evaluation as acetylcholinesterase inhibitors

Bioorg Med Chem Lett. 2005 Jun 2;15(11):2711-5. doi: 10.1016/j.bmcl.2005.04.005.

Authors

Darío A Bianchi¹, Guillermo Schmeda Hirschmann, Cristina Theoduloz, Andrea B J Bracca, Teodoro S Kaufman

Affiliation

¹ Instituto de Química Orgánica de Síntesis (CONICET-UNR) and Facultad de Ciencias Bioquímicas y Farmacéuticas, Universidad Nacional de Rosario, Argentina.

PMID: 15878275
DOI: 10.1016/j.bmcl.2005.04.005

Abstract

The synthesis of simplified analogs of the novel isoquinoline alkaloid stephaoxocanidine, carrying the oxazaphenalene ABC-ring system of the natural product, and their activity as inhibitors of the enzyme acetylcholinesterase, are reported. 5,6-Dimethoxy-7H -8-oxa-1-aza-phenalen-9-one (5) was as active as a Narcissus extract enriched in galantamine.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Acetylcholinesterase / drug effects*
Cholinesterase Inhibitors / chemical synthesis*
Cholinesterase Inhibitors / pharmacology*
Drug Evaluation, Preclinical
Isoquinolines / chemical synthesis*
Isoquinolines / pharmacology*

Substances

Cholinesterase Inhibitors
Isoquinolines
stephaoxocanidine
Acetylcholinesterase