exo-2-(pyridazin-4-yl)-7-azabicyclo[2.2.1]heptanes: Syntheses and nicotinic acetylcholine receptor agonist activity of potent pyridazine analogues of (±)-epibatidine

Journal of Medicinal Chemistry

Volumn 44, Issue 1, 2001, Pages 47-57

  Che, D ^a   Wegge, T ^a   Stubbs, M T ^a   Seitz, G ^a   Meier, H ^b   Methfessel, C ^b  

^a PHILIPPS UNIVERSITY MARBURG   (Germany)

^b BAYER AG   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

EPIBATIDINE; EXO 2 (3,6 BISTRIFLUOROMETHYLPYRIDAZIN 4 YL) 7 AZABICYCLO[2.2.1]HEPTANE; EXO 2 (3,6 DICHLOROPYRIDAZIN 4 YL) 7 AZABICYCLO[2.2.1]HEPTANE 7 CARBOXYLIC ACID ETHYL ESTER; EXO 2 (PYRIDAZIN 4 YL) 7 AZABICYCLO[2.2.1]HEPTANE; EXO 2 (PYRIDAZIN 4 YL) 7 AZABICYCLO[2.2.1]HEPTANE CARBOXYLIC ACID ETHYL ESTER; EXO 7 ACETYL 2 (PYRIDAZIN 4 YL) 7 AZABICYCLO[2.2.1]HEPTANE; EXO 7 METHYL 2 (PYRIDAZIN 4 YL) 7 AZABICYCLO[2.2.1]HEPTANE; N (3 PYRIDAZIN 4 YLCYCLOHEX 3 ENYL)ACETAMIDE; NICOTINIC AGENT; NORBORNANE DERIVATIVE; PYRIDAZINE DERIVATIVE; TETRAZINE DERIVATIVE; UNCLASSIFIED DRUG;

ANIMAL CELL; ARTICLE; CRYSTAL STRUCTURE; DRUG ACTIVITY; DRUG POTENCY; DRUG SELECTIVITY; DRUG SYNTHESIS; ELECTRON; IN VITRO STUDY; NONHUMAN; PROTEIN CONFORMATION; X RAY CRYSTALLOGRAPHY; XENOPUS;

ANIMALS; BICYCLO COMPOUNDS, HETEROCYCLIC; CRYSTALLOGRAPHY, X-RAY; LIGANDS; NICOTINIC AGONISTS; OOCYTES; PATCH-CLAMP TECHNIQUES; PYRIDAZINES; PYRIDINES; RATS; STEREOISOMERISM; XENOPUS LAEVIS;

EID: 0035804307     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm000949w     Document Type: Article

References (49)

1. Epibatidine: A novel (Chloropyridyl)azabicycloheptane with potent analgesic activity from an Ecuadoran poison frog
2. Total synthesis and determination of the absolute configuration of epibatidine
3. Epibatidine, a potent-analgetic and nicotinic agonist
4. Epibatidine: Pharmacological properties of a novel nicotinic acetylcholine receptor agonist and analgesic agent
5. Epibatidine: Discovery and definition as a potent analgesic and nicotinic agonist
6. Epibatidine and pain
7. Therapeutic potential of neuronal nicotinic acetylcholine receptor agonists as novel analgesics
8. Chemistry of 7-azabicyclo[22.1]hepta-2,5-diens, 7-azabicyclo[2.2.1]hept-2-enes, and 7-azabicyclo[2.2.1]-heptanes
9. Synthetic approaches to epibatidine
10. Epibatidine
11. The epibatidine competition: Synthetic work on a novel natural analgetic
12. Epibatidin - Ein nicotinartiges, analgetisch wirksames Alkaloid aus Pfeilgiftfröschen
13. Epibatidine
14. α-Iodocycloalkenones: Synthesis of (±)-epibatidine
15. A versatile and stereoselective synthesis of (±)-epibatidine
16. Formal synthesis of natural epibatidine and of its enantiomer: Use of radical cyclization in an enantiospecific route
17. New synthesis of 7-(tert-butoxycarbonyl)-7-azabicyclo[2.2.1]hept-2-ene. A key intermediate in the synthesis of epibatidine and analogues
18. New asymmetric transformation of optically active allene-1,3-dicarboxylate and its application to the formal asymmetric synthesis of (-)epibatidine
19. Total synthesis of (-)-epibatidine using an asymmetric diels - Alder-reaction with a chiral N-acylnitroso dienophile
20. 2-(Het)aryl-substituted 7-Azabicyclo[2-2-1]-heptane systems
21. Palladium(II)-Catalyzed 1,4-oxidation of 2-aryl-1,3-cyclohexadienes. Application to the synthesis of (±)-epibatidine and analogues
22. 2-Bromoethynyl aryl sulfones as versatile dienophiles: A formal synthesis of epibatidine
23. Synthesis and analgesic activity of epibatidine analogues
24. Synthesis of epibatidine homologues: Homoepibatidine and bis-homoepitbatidine
25. Synthesis of (±)-epibatidine and its analogues
26. Synthesis of optically pure epibatidine analogues: (1R,2R,5S)-2β-(2-Chloro-5-pyridinyl)-8-azabicyclo[3.2.1]loctane and (1R,2S,5S)-2α-(2-chloro-5-pyridinyl)-8-azabicyclo[3.2.1]octane from (-)-cocaine
27. Synthesis of UB-165: A novel nicotinic ligand and anatoxina/epibatidine hybrid
28. Synthesis and nicotinic activity of epiboxidine: An isoxazole analogue of epibatidine
29. Synthesis and structure - Activity data of some new epibatidine analogues
30. Synthesis of chiral 2-(2′-pyrrolidinyl)pyridines from (S)-and (R)-proline: Potential ligands of the neuronal nicotinic acetylcholine receptors
31. 1,2,4,5-Tetrazines
32. Trimethylsilyl iodide as a peptide deblocking agent
33. A theoretical study of epibatidine
34. Epibatidine-aided studies toward definition of a nicotine receptor pharmakophore
35. Neuronal nicotinic acetylcholine receptors as targets for drug discovery
36. Recent developments in neuronal nicotinic acetylcholine receptor modulators
37. 2-, 5- and 6-Halo-3-2(-(S)azetidinylmethoxylpyridines: Synthesis, affinity for nicotinic acetylcholine receptors, and molecular modeling
38. The ensemble approach to distance geometry: Application to the nicotinic pharmacophore
39. Pentafluorophenyl acetate: A new, highly selective acetylating agent
40. Pentafluorophenyl esters of dicarboxylic acids
41. Solvent effects on the barrier to rotation in carbamates
42. 11C] methylated analogues of epibatidine as tracers for positron emission tomographic studies of nicotinic acetylcholine receptors
43. Pharmcology of the nicotinic acetylcholine receptor from fetal rat muscle expressed in Xenopus oocytes
44. Completion and refinement of crystal structures with SIR92