Synthesis, nicotinic acetylcholine receptor binding, and antinociceptive properties of 2-exo-2-(2′-substituted 5′-pyridinyl)-7-azabicyclo[2.2.1]heptanes. Epibatidine analogues

Journal of Medicinal Chemistry

Volumn 44, Issue 13, 2001, Pages 2229-2237

  Carroll, F I ^a   Liang, F ^a   Navarro, H A ^a   Brieaddy, L E ^a   Abraham, P ^a   Damaj, M I ^b   Martin, B R ^b  

^a RTI INTERNATIONAL   (United States)

^b VIRGINIA COMMONWEALTH UNIVERSITY SCHOOL OF MEDICINE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

7 TERT BUTOXYCARBONYL 2 EXO (2' AMINO 5' PYRIDINYL) 7 AZABICYCLO[2.2.1]HEPTANE; 7 TERT BUTOXYCARBONYL 7 AZABICYCLO[2.2.1]HEPT 2 ENE; ALKENE; AMINE; BROMINE; CYCLOHEPTANE DERIVATIVE; EPIBATIDINE; FLUORINE; HYDROGEN; HYDROXYL GROUP; IODINE; METHYLLYCACONITINE; NICOTINE; NICOTINIC AGENT; NICOTINIC RECEPTOR; PYRIDINE DERIVATIVE; TETRABUTYLAMMONIUM; TRIBUTYLTIN; TRIFLUOROMETHANESULFONIC ACID; UNCLASSIFIED DRUG;

ADOLESCENT; ANIMAL EXPERIMENT; ANIMAL TISSUE; ANTINOCICEPTION; ARTICLE; BINDING AFFINITY; CONTROLLED STUDY; DOSE RESPONSE; MALE; MOUSE; NONHUMAN; RECEPTOR BINDING; STRUCTURE ACTIVITY RELATION; SYNTHESIS; TAIL FLICK TEST;

ANALGESICS, NON-NARCOTIC; ANIMALS; BICYCLO COMPOUNDS, HETEROCYCLIC; BINDING, COMPETITIVE; CEREBRAL CORTEX; MALE; MICE; MICE, INBRED ICR; PAIN MEASUREMENT; PYRIDINES; RADIOLIGAND ASSAY; RATS; REACTION TIME; RECEPTORS, NICOTINIC; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 0035927437     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm0100178     Document Type: Article

References (28)

1. Natural products as a source of nicotinic acetylcholine receptor modulators and leads for drug discovery
2. Synthesis and nicotinic acetylcholine receptor binding properties of exo-2-(2′-fluoro-5′-pyridinyl)-7-azabicyclo[2.2.1]heptane: A new positron emission tomography ligand for nicotinic receptors
3. Nicotinic acetylcholine receptor-targeted compounds: A summary of the development pipeline and therapeutic potential
4. Central nicotinic receptor ligands and pharmacophores
5. Neuronal nicotinic acetylcholine receptors as targets for drug discovery
6. Neuronal nicotinic acetylcholine receptors as novel drug targets
7. Mapping nicotinic acetylcholine receptors with PET
8. 18F]norchlorofluoroepibatidine and its N-methyl derivative: New PET ligands for mapping nicotinic acetylcholine receptors
9. 18F]N-methyl-NFEP: Kinetics, nicotine effect, and toxicity
10. 18F]fluoronorchloroepibatidine in rodent and human brain
11. In vivo labeling of neuronal nicotinic acetylcholine receptors with radiolabeled isomers of norchloroepibatidine
12. 125I]IPH, an epibatidine analog, binds with high affinity to neuronal nicotinic cholinergic receptors
13. Total synthesis of (±)-epibatidine
14. A total synthesis of (±)-epibatidine
15. Synthesis of (+)- and (-)-epibatidine
16. New synthesis of 7-(tert-butoxycarbonyl)-7-azabicyclo [2.2.1]hept-2-ene. A key intermediate in the synthesis of epibatidine and analogs
17. Synthesis and σ binding properties of 2′-substituted 5,9α-dimethyl-6,7-benzomorphans
18. Total synthesis and determination of the absolute configuration of epibatidine
19. 50) of an enzymatic reaction
20. 7 nicotinic acetylcholine receptor
21. Intrathecal morphine in mice: A new technique
22. A method for determining loss of pain sensation
23. Epibatidine, a potent analgetic and nicotinic agonist
24. 3H]epibatidine binding to nicotinic cholinergic receptors in rat and human brain
25. 3H]epibatidine to rat brain membranes
26. 11C]methylated analogues of epibatidine as tracers for positron emission tomographic studies of nicotinic acetylcholine receptors
27. Synthesis, receptor binding and QSAR studies on 6-substituted nicotine derivatives as cholinergic ligands