AM-630

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AM-630
(IUPAC) ime
1-[2-(morfolin-4-il)etil]-2-metil-3-(4-metoksibenzoil)-6-jodoindol
Klinički podaci
Identifikatori
CAS broj 164178-33-0
ATC kod nije dodeljen
PubChem[1][2] 4302963
ChemSpider[3] 3508738
ChEMBL[4] CHEMBL181633 YesY
Hemijski podaci
Formula C23H25IN2O3 
Mol. masa 504,360 g/mol
SMILES eMolekuli & PubHem
Farmakoinformacioni podaci
Trudnoća ?
Pravni status

AM-630 (6-Jodopravadolin) je lek koji deluje kao potentan i selektivan inverzni agonist za kanabinoidni receptor CB2, sa Ki od 32,1 nM na CB2 i 165x selektivnošću u odnosu na CB1, na kome deluje kao slab parcijalni agonist.[5] On se koristi u istraživanju CB2 posredovanih responsa i korišten je za istraživanje moguće uloge CB2 receptora u mozgu.[6][7] AM-630 je značajan kao jedan od prvih indolnih kanabinoidnih liganda supstituisanih na 6-poziciji indolnog prstena, za koju je naknadno utvrđena da je važna u određivanju afiniteta i efikasnosti na CB1 i CB2 receptorima. To je dovelo do razvoja znatnog broja srodnih jedinjenja.[8][9][10][11][12]

Reference[uredi - уреди | uredi izvor]

  1. Li Q, Cheng T, Wang Y, Bryant SH (2010). "PubChem as a public resource for drug discovery.". Drug Discov Today 15 (23-24): 1052–7. PMID 20970519. doi:10.1016/j.drudis.2010.10.003.  edit
  2. Evan E. Bolton, Yanli Wang, Paul A. Thiessen, Stephen H. Bryant (2008). "Chapter 12 PubChem: Integrated Platform of Small Molecules and Biological Activities". Annual Reports in Computational Chemistry 4: 217–241. doi:10.1016/S1574-1400(08)00012-1. 
  3. Hettne KM, Williams AJ, van Mulligen EM, Kleinjans J, Tkachenko V, Kors JA. (2010). "Automatic vs. manual curation of a multi-source chemical dictionary: the impact on text mining". J Cheminform 2 (1): 3. PMID 20331846. doi:10.1186/1758-2946-2-3.  edit
  4. Gaulton A, Bellis LJ, Bento AP, Chambers J, Davies M, Hersey A, Light Y, McGlinchey S, Michalovich D, Al-Lazikani B, Overington JP. (2012). "ChEMBL: a large-scale bioactivity database for drug discovery". Nucleic Acids Res 40 (Database issue): D1100–7. PMID 21948594. doi:10.1093/nar/gkr777.  edit
  5. Ross RA, Brockie HC, Stevenson LA, Murphy VL, Templeton F, Makriyannis A, Pertwee RG (February 1999). "Agonist-inverse agonist characterization at CB1 and CB2 cannabinoid receptors of L759633, L759656, and AM630". British Journal of Pharmacology 126 (3): 665–72. PMC 1565857. PMID 10188977. doi:10.1038/sj.bjp.0702351. 
  6. Morgan NH, Stanford IM, Woodhall GL (September 2009). "Functional CB2 type cannabinoid receptors at CNS synapses". Neuropharmacology 57 (4): 356–68. PMID 19616018. doi:10.1016/j.neuropharm.2009.07.017. 
  7. Ishiguro H, Horiuchi Y, Ishikawa M, Koga M, Imai K, Suzuki Y, Morikawa M, Inada T, Watanabe Y, Takahashi M, Someya T, Ujike H, Iwata N, Ozaki N, Onaivi ES, Kunugi H, Sasaki T, Itokawa M, Arai M, Niizato K, Iritani S, Naka I, Ohashi J, Kakita A, Takahashi H, Nawa H, Arinami T (May 2010). "Brain cannabinoid CB2 receptor in schizophrenia". Biological Psychiatry 67 (10): 974–82. PMID 19931854. doi:10.1016/j.biopsych.2009.09.024. 
  8. Eissenstat, M. A.; Bell, M. R.; D'ambra, T. E.; Alexander, E. J.; Daum, S. J.; Ackerman, J. H.; Gruett, M. D.; Kumar, V.; Estep, K. G. (1995). "Aminoalkylindoles: Structure-Activity Relationships of Novel Cannabinoid Mimetics". Journal of Medicinal Chemistry 38 (16): 3094. PMID 7636873. doi:10.1021/jm00016a013. 
  9. Hongfeng Deng. Design and synthesis of selective cannabinoid receptor ligands: Aminoalkylindole and other heterocyclic analogs. PhD Dissertation, University of Connecticut, 2000.
  10. Hynes J, Leftheris K, Wu H, Pandit C, Chen P, Norris DJ, Chen BC, Zhao R, Kiener PA, Chen X, Turk LA, Patil-Koota V, Gillooly KM, Shuster DJ, McIntyre KW (September 2002). "C-3 Amido-indole cannabinoid receptor modulators". Bioorganic & Medicinal Chemistry Letters 12 (17): 2399–402. PMID 12161142. doi:10.1016/S0960-894X(02)00466-3. 
  11. Frost, J. M.; Dart, M. J.; Tietje, K. R.; Garrison, T. R.; Grayson, G. K.; Daza, A. V.; El-Kouhen, O. F.; Miller, L. N.; Li, L. (2008). "Indol-3-yl-tetramethylcyclopropyl Ketones: Effects of Indole Ring Substitution on CB2 Cannabinoid Receptor Activity". Journal of Medicinal Chemistry 51 (6): 1904. PMID 18311894. doi:10.1021/jm7011613. 
  12. Adam, J. M.; Cairns, J.; Caulfield, W.; Cowley, P.; Cumming, I.; Easson, M.; Edwards, D.; Ferguson, M.; Goodwin, R. (2010). "Design, synthesis, and structure–activity relationships of indole-3-carboxamides as novel water soluble cannabinoid CB1 receptor agonists". MedChemComm 1: 54. doi:10.1039/c0md00022a. 

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