title: Synthesis and AChE inhibitory activity of new chiral tetrahydroacridine analogues from terpenic cyclanones.
abstract: This work describes the enantioselective synthesis of a new series of terpenic chiral 9-aminotetrahydroacridine analogues. Several chiral ketones were synthesized from natural monoterpenes in an optically active form and subjected to the cyclodehydration reactions with anthranilonitrile in the presence of BF(3).Et(2)O as catalyst. The 9-aminotetrahydroacridine analogues were tested as acetylcholinesterase (AChE) inhibitors. Based on qualitative structure-activity relationship some trends are suggested.
authors: Instituto de Química, Universidade Federal do Rio Grande do Sul, Av Bento Gonçalves, 9500 Campus do Vale, 91501-970 Porto Alegre, RS, Brazil.
authors: Diego
authors: D
authors: dos Santos Pisoni
authors: Jessé
authors: J
authors: Sobieski da Costa
authors: Douglas
authors: D
authors: Gamba
authors: Cesar Liberato
authors: CL
authors: Petzhold
authors: Antonio César
authors: AC
authors: de Amorim Borges
authors: Marco Antonio
authors: MA
authors: Ceschi
authors: Paula
authors: P
authors: Lunardi
authors: Carlos Alberto
authors: CA
authors: Saraiva Gonçalves
mesh_terms: D000110:Acetylcholinesterase / Q000378:metabolism*; D000166:Acridines / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D000818:Animals; D001880:Boranes / Q000737:chemistry; D002384:Catalysis; D002800:Cholinesterase Inhibitors / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D008297:Male; D009570:Nitriles / Q000737:chemistry; D051381:Rats; D017208:Rats, Wistar; D013237:Stereoisomerism; D013729:Terpenes / Q000737:chemistry*
chemical_list: D000166:Acridines; D001880:Boranes; D002800:Cholinesterase Inhibitors; D009570:Nitriles; D013729:Terpenes; C021274:boron trifluoride; D000110:Acetylcholinesterase