Synthesis and AChE inhibitory activity of new chiral tetrahydroacridine analogues from terpenic cyclanones.
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.
dos Santos Pisoni
Diego
D
Instituto de Química, Universidade Federal do Rio Grande do Sul, Av Bento Gonçalves, 9500 Campus do Vale, 91501-970 Porto Alegre, RS, Brazil.
Sobieski da Costa
Jessé
J
Gamba
Douglas
D
Petzhold
Cesar Liberato
CL
de Amorim Borges
Antonio César
AC
Ceschi
Marco Antonio
MA
Lunardi
Paula
P
Saraiva Gonçalves
Carlos Alberto
CA
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*
D000166:Acridines; D001880:Boranes; D002800:Cholinesterase Inhibitors; D009570:Nitriles; D013729:Terpenes; C021274:boron trifluoride; D000110:Acetylcholinesterase