title: First total synthesis of (+/-)-3-hydroxy-11-norcytisine: structure confirmation and biological characterization.
abstract: The first total synthesis of the natural product 3-hydroxy-11-norcytisine (1), structurally related to cytisine (2), a benchmark ligand at neuronal nicotinic acetylcholine receptors (NNRs), has been achieved. The synthesis permits the unambiguous confirmation of the structure originally proposed for 1 and has enabled initial biological characterization of 1 and its related compounds against NNRs.
authors.affiliation: Targacept, Inc., 200 East First Street, Suite 300, Winston-Salem, North Carolina 27101, USA. daniel.yohannes@targacept.com
authors.forename: Daniel
authors.initials: D
authors.lastname: Yohannes
authors.forename: Camilla P
authors.initials: CP
authors.lastname: Hansen
authors.forename: Srinivasa Rao
authors.initials: SR
authors.lastname: Akireddy
authors.forename: Terry A
authors.initials: TA
authors.lastname: Hauser
authors.forename: Melanie N
authors.initials: MN
authors.lastname: Kiser
authors.forename: Nicholas J
authors.initials: NJ
authors.lastname: Gurnon
authors.forename: Cynthia S
authors.initials: CS
authors.lastname: Day
authors.forename: Balwinder
authors.initials: B
authors.lastname: Bhatti
authors.forename: William S
authors.initials: WS
authors.lastname: Caldwell
mesh_terms: D000470:Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry / Q000378:metabolism*; D000818:Animals; D001392:Azocines / Q000138:chemical synthesis / Q000737:chemistry / Q000378:metabolism; D009682:Magnetic Resonance Spectroscopy; D011807:Quinolizines / Q000138:chemical synthesis / Q000737:chemistry / Q000378:metabolism; D051381:Rats; D011978:Receptors, Nicotinic / Q000378:metabolism; D064569:alpha7 Nicotinic Acetylcholine Receptor; D000093843:Quinolizidine Alkaloids
chemical_list: D000470:Alkaloids; D001392:Azocines; D011807:Quinolizines; D011978:Receptors, Nicotinic; D064569:alpha7 Nicotinic Acetylcholine Receptor; C579165:Chrna7 protein, rat; C403531:nicotinic receptor alpha4beta2; C004712:cytisine; D000093843:Quinolizidine Alkaloids