TY - JOUR
T1 - Synthesis and Chemical Resolution of a Novel Class of Rigid 1-(1-Phenylcyclohexyl)-iperidine(PCP) Analogues
AU - Kozikowski, Alan P.
AU - Pang, Yuan Ping
N1 - Publisher Copyright:
© 1990 Georg Thieme Verlag. All rights reserved.
PY - 1990/1
Y1 - 1990/1
N2 - A novel class of conformationally rigidified phencyclidine (1-(1-phenylcyclohexyl)piperidine; PCP) analogues-4a-amino-1,4,4a,9a-tetrahydrofluorenes 1, 2, 5, 6 and 4a-amino-1,2,3,4,4a,9a-hexahydrofluorenes 3, 4, 7, 8-has been prepared through a Diels-Alder approach and resolved by aid of (+)- A nd (-)-tartaric acid. One member of this series, the (4aR, 9aS)-4a-amino derivative 3, was found to exhibit a high affinity (IC 50 = 19 nm) for the PCP recognition site in the brain, thus allowing a more rigorous assignment of the conformation of PCP relevant to binding at these sites.
AB - A novel class of conformationally rigidified phencyclidine (1-(1-phenylcyclohexyl)piperidine; PCP) analogues-4a-amino-1,4,4a,9a-tetrahydrofluorenes 1, 2, 5, 6 and 4a-amino-1,2,3,4,4a,9a-hexahydrofluorenes 3, 4, 7, 8-has been prepared through a Diels-Alder approach and resolved by aid of (+)- A nd (-)-tartaric acid. One member of this series, the (4aR, 9aS)-4a-amino derivative 3, was found to exhibit a high affinity (IC 50 = 19 nm) for the PCP recognition site in the brain, thus allowing a more rigorous assignment of the conformation of PCP relevant to binding at these sites.
UR - http://www.scopus.com/inward/record.url?scp=84918615669&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=84918615669&partnerID=8YFLogxK
U2 - 10.1055/s-1990-20989
DO - 10.1055/s-1990-20989
M3 - Article
AN - SCOPUS:84918615669
SN - 0936-5214
VL - 1990
SP - 58
EP - 63
JO - Synlett
JF - Synlett
IS - 1
ER -