Probes for narcotic receptor mediated phenomena. 40. N-substituted cis-4a-ethyl-1,2,3,4,4a,9a-hexahydrobenzofuro[2,3-c]pyridin-8-ols.
A series of N-substituted rac-cis-4a-ethyl-1,2,3,4,4a,9a-hexahydrobenzofuro[2,3-c]pyridin-8-ols have been prepared using a simple synthetic route previously designed for synthesis of related cis-2-methyl-4a-alkyl-1,2,3,4,4a,9a-hexahydrobenzofuro[2,3-c]pyridin-6-ols. The new phenolic compounds, where the aromatic hydroxy moiety is situated ortho to the oxygen atom in the oxide-bridged ring, do not interact as well as the pyridin-6-ols with opioid receptors. The N-para-fluorophenethyl derivative had the highest mu-opioid receptor affinity of the examined compounds (K(i)=0.35 microM).
Iyer
Malliga R
MR
Drug Design and Synthesis Section, Department of Health and Human Services, Chemical Biology Research Branch, National Institute on Drug Abuse and the National Institute on Alcohol Abuse and Alcoholism, National Institutes of Health, 5625 Fishers Lane, Room 4N03, Bethesda, MD 20892-9415, USA.
Lee
Yong Sok
YS
Deschamps
Jeffrey R
JR
Rothman
Richard B
RB
Dersch
Christina M
CM
Jacobson
Arthur E
AE
Rice
Kenner C
KC
D000818:Animals; D001572:Benzofurans / Q000737:chemistry* / Q000494:pharmacology*; D016466:CHO Cells; D006224:Cricetinae; D003412:Cricetulus; D018360:Crystallography, X-Ray; D008958:Models, Molecular; D015394:Molecular Structure; D011485:Protein Binding; D011725:Pyridines / Q000737:chemistry* / Q000494:pharmacology*; D011957:Receptors, Opioid / Q000737:chemistry / Q000378:metabolism*
D001572:Benzofurans; D011725:Pyridines; D011957:Receptors, Opioid; C548793:cis-4a-ethyl-1,2,3,4,4a,9a-hexahydrobenzofuro(2,3-c)pyridin-8-ol