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AR-R17779

From Wikipedia, the free encyclopedia
AR-R17779
Names
IUPAC name
(2S)-4′-Azaspiro[bicyclo[2.2.2]octane-2,5′-[1,3]oxazolidin]-2′-one
Other names
(−)-Spiro[1-azabicyclo[2.2.2]octane-3,5′-oxazolidin-2′-one]
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
UNII
  • InChI=1S/C9H14N2O2/c12-8-10-5-9(13-8)6-11-3-1-7(9)2-4-11/h7H,1-6H2,(H,10,12)/t9-/m0/s1 checkY
    Key: TYAGAVRSOFABFO-VIFPVBQEBZ ☒N
  • InChI=1/C9H14N2O2/c12-8-10-5-9(13-8)6-11-3-1-7(9)2-4-11/h7H,1-6H2,(H,10,12)/t9-/m0/s1
  • O=C3O[C@]1(CN2CCC1CC2)CN3
Properties
C9H14N2O2
Molar mass182.223 g·mol−1
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)
Chemical compound

AR-R17779 is a drug that acts as a potent and selectivefull agonist for theα7 subtype of neuralnicotinic acetylcholine receptors.[1][2] It hasnootropic effects in animal studies,[3][4] but its effects do not substitute for those ofnicotine.[5] It has also been studied as a potential novel treatment forarthritis.[6]

References

[edit]
  1. ^Mullen, G.; Napier, A.; Balestra, M.; Decory, T.; Hale, G.; Macor, J.; Mack, R.; Loch, J.; Wu, E.; Kover, A.; Verhoest, P.; Sampognaro, A.; Phillips, E.; Zhu, Y.; Murray, R.; Griffith, R.; Blosser, J.; Gurley, D.; Machulskis, A.; Zongrone, J.; Rosen, A.; Gordon, J. (2000). "(−)-Spiro[1-azabicyclo[2.2.2]octane-3,5′-oxazolidin-2′-one], a conformationally restricted analogue of acetylcholine, is a highly selective full agonist at the α7 nicotinic acetylcholine receptor".Journal of Medicinal Chemistry.43 (22):4045–4050.doi:10.1021/jm000249r.PMID 11063601.
  2. ^Macor, J.; Mullen, G.; Verhoest, P.; Sampognaro, A.; Shepardson, B.; Mack, R. (2004). "A chiral synthesis of (−)-spiro[1-azabicyclo[2.2.2]octane-3,5′-oxazolidin-2′-one]: A conformationally restricted analogue of acetylcholine that is a potent and selective α7 nicotinic receptor agonist".The Journal of Organic Chemistry.69 (19):6493–6495.doi:10.1021/jo049404q.PMID 15357617.
  3. ^Levin, E. D.; Bettegowda, C.; Blosser, J.; Gordon, J. (1999). "AR-R 17779, an α7 nicotinic agonist, improves learning and memory in rats".Behavioural Pharmacology.10 (6–7):675–680.doi:10.1097/00008877-199911000-00014.PMID 10780509.
  4. ^Van Kampen, M.; Selbach, K.; Schneider, R.; Schiegel, E.; Boess, F.; Schreiber, R. (2004). "AR-R 17779 improves social recognition in rats by activation of nicotinic α7 receptors".Psychopharmacology.172 (4):375–383.doi:10.1007/s00213-003-1668-7.PMID 14727003.S2CID 23423717.
  5. ^Grottick, A. J.; Trube, G.; Corrigall, W. A.; Huwyler, J.; Malherbe, P.; Wyler, R.; Higgins, G. A. (2000). "Evidence that nicotinic α7 receptors are not involved in the hyperlocomotor and rewarding effects of nicotine".The Journal of Pharmacology and Experimental Therapeutics.294 (3):1112–1119.doi:10.1016/S0022-3565(24)39179-7.PMID 10945867.
  6. ^Van Maanen, M.; Lebre, M.; Van Der Poll, T.; Larosa, G.; Elbaum, D.; Vervoordeldonk, M.; Tak, P. (2009)."Stimulation of nicotinic acetylcholine receptors attenuates collagen-induced arthritis in mice".Arthritis and Rheumatism.60 (1):114–122.doi:10.1002/art.24177.PMID 19116908.
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nAChRsTooltip Nicotinic acetylcholine receptors
Agonists
(andPAMsTooltip positive allosteric modulators)
Antagonists
(andNAMsTooltip negative allosteric modulators)
Precursors
(andprodrugs)


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