bradanicline   

GtoPdb Ligand ID: 3969

Synonyms: compound 7a [PMID 23126648] [3] | TC-5619 | TC5619
Compound class: Synthetic organic
Comment: Bradanicline is an investigational agonist of neuronal α7 subunit-containing nicotinic acetylcholine receptors [3].
2D Structure
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Physico-chemical Properties
Hydrogen bond acceptors 4
Hydrogen bond donors 1
Rotatable bonds 5
Topological polar surface area 58.37
Molecular weight 361.18
XLogP 2.55
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
Canonical SMILES O=C(c1cc2c(o1)cccc2)NC1C2CCN(C1Cc1cccnc1)CC2
Isomeric SMILES O=C(c1cc2c(o1)cccc2)N[C@@H]1C2CCN([C@H]1Cc1cccnc1)CC2
InChI InChI=1S/C22H23N3O2/c26-22(20-13-17-5-1-2-6-19(17)27-20)24-21-16-7-10-25(11-8-16)18(21)12-15-4-3-9-23-14-15/h1-6,9,13-14,16,18,21H,7-8,10-12H2,(H,24,26)/t18-,21+/m0/s1
InChI Key OXKRFEWMSWPKKV-GHTZIAJQSA-N
References
1. Hauser TA, Kucinski A, Jordan KG, Gatto GJ, Wersinger SR, Hesse RA, Stachowiak EK, Stachowiak MK, Papke RL, Lippiello PM et al.. (2009)
TC-5619: an alpha7 neuronal nicotinic receptor-selective agonist that demonstrates efficacy in animal models of the positive and negative symptoms and cognitive dysfunction of schizophrenia.
Biochem. Pharmacol., 78 (7): 803-12. [PMID:19482012]
2. Lieberman JA, Dunbar G, Segreti AC, Girgis RR, Seoane F, Beaver JS, Duan N, Hosford DA. (2013)
A randomized exploratory trial of an α-7 nicotinic receptor agonist (TC-5619) for cognitive enhancement in schizophrenia.
Neuropsychopharmacology, 38 (6): 968-75. [PMID:23303043]
3. Mazurov AA, Kombo DC, Hauser TA, Miao L, Dull G, Genus JF, Fedorov NB, Benson L, Sidach S, Xiao Y et al.. (2012)
Discovery of (2S,3R)-N-[2-(pyridin-3-ylmethyl)-1-azabicyclo[2.2.2]oct-3-yl]benzo[b]furan-2-carboxamide (TC-5619), a selective α7 nicotinic acetylcholine receptor agonist, for the treatment of cognitive disorders.
J. Med. Chem., 55 (22): 9793-809. [PMID:23126648]