title: Heteropoly acid-catalyzed microwave-assisted three-component aza-Diels-Alder cyclizations: diastereoselective synthesis of potential drug candidates for Alzheimer's disease.
abstract: A highly diastereoselective microwave-assisted three component synthesis of azabicyclo[2.2.2]octan-5-ones by a silicotungstic acid-catalyzed aza-Diels-Alder cyclization is described. The one-pot process involves the formation of the in situ generated Schiff base and its immediate cyclization with cyclohex-2-enone. The short reaction times, good yields and excellent diastereoselectivity make this annulation a practical and environmentally attractive method for the synthesis of the target compounds. Preliminary assays were carried out to determine the activity of the products in AChE as well as in amyloid β fibrillogenesis inhibition.
authors.affiliation: Department of Chemistry, University of Massachusetts Boston, 100 Morrissey Blvd., Boston, MA 02125, USA.
authors.forename: Dmitry
authors.initials: D
authors.lastname: Borkin
authors.forename: Elena
authors.initials: E
authors.lastname: Morzhina
authors.forename: Silpi
authors.initials: S
authors.lastname: Datta
authors.forename: Aleksandra
authors.initials: A
authors.lastname: Rudnitskaya
authors.forename: Abha
authors.initials: A
authors.lastname: Sood
authors.forename: Marianna
authors.initials: M
authors.lastname: Török
authors.forename: Béla
authors.initials: B
authors.lastname: Török
mesh_terms: D000110:Acetylcholinesterase / Q000737:chemistry / Q000378:metabolism; D000143:Acids / Q000737:chemistry*; D000544:Alzheimer Disease / Q000188:drug therapy / Q000378:metabolism*; D016229:Amyloid beta-Peptides / Q000378:metabolism; D001372:Aza Compounds / Q000737:chemistry*; D002384:Catalysis; D002800:Cholinesterase Inhibitors / Q000737:chemistry / Q000494:pharmacology; D003500:Cyclization; D006801:Humans; D008872:Microwaves; D015394:Molecular Structure; D013237:Stereoisomerism
chemical_list: D000143:Acids; D016229:Amyloid beta-Peptides; D001372:Aza Compounds; D002800:Cholinesterase Inhibitors; D000110:Acetylcholinesterase