AR-R17779

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 X markN
  • 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 mass 182.223 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
X markN verify (what is checkYX markN ?)

AR-R17779 is a drug that acts as a potent and selective full agonist for the α7 subtype of neural nicotinic acetylcholine receptors. It has nootropic effects in animal studies, but its effects do not substitute for those of nicotine. It has also been studied as a potential novel treatment for arthritis.

References

  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.