First total synthesis of (+/-)-3-hydroxy-11-norcytisine: structure confirmation and biological characterization.
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.
Yohannes
Daniel
D
Targacept, Inc., 200 East First Street, Suite 300, Winston-Salem, North Carolina 27101, USA. daniel.yohannes@targacept.com
Hansen
Camilla P
CP
Akireddy
Srinivasa Rao
SR
Hauser
Terry A
TA
Kiser
Melanie N
MN
Gurnon
Nicholas J
NJ
Day
Cynthia S
CS
Bhatti
Balwinder
B
Caldwell
William S
WS
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
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