ZY7

(3E)-3-[(2,4-DIMETHOXYPHENYL)METHYLIDENE]-3,4,5,6-TETRAHYDRO-2,3'-BIPYRIDINE


Toggle HydrogenToggle Labels

Chemical Component Summary

Name(3E)-3-[(2,4-DIMETHOXYPHENYL)METHYLIDENE]-3,4,5,6-TETRAHYDRO-2,3'-BIPYRIDINE
Identifiers3-[(3E)-3-[(2,4-dimethoxyphenyl)methylidene]-5,6-dihydro-4H-pyridin-2-yl]pyridine
FormulaC19 H20 N2 O2
Molecular Weight308.374
TypeNON-POLYMER
Isomeric SMILESCOc1ccc(c(c1)OC)\C=C\2/CCCN=C2c3cccnc3
InChIInChI=1S/C19H20N2O2/c1-22-17-8-7-14(18(12-17)23-2)11-15-5-4-10-21-19(15)16-6-3-9-20-13-16/h3,6-9,11-13H,4-5,10H2,1-2H3/b15-11+
InChIKeyRPYWXZCFYPVCNQ-RVDMUPIBSA-N

Chemical Details

Formal Charge0
Atom Count43
Chiral Atom Count0
Bond Count45
Aromatic Bond Count12

Drug Info: DrugBank

DrugBank IDDB05708 
NameGTS-21
Groups investigational
DescriptionGTS-21 (also known as DMBX-A), is a novel, small-molecule, orally active and selective alpha-7 nicotinic acetylcholine (nACh) receptor agonist that has demonstrated memory and cognition enhancement activity in human clinical trials. Athenagen licensed the exclusive rights to the compound and a related library of analogs as part of the acquisition of Osprey Pharmaceutical Company in April 2006. GTS-21 has been studied in multiple Phase I studies in healthy volunteers and one Phase I/II study in schizophrenic patients. In all studies, the compound was well tolerated. In a Phase I multi-dose, double-blind, placebo controlled study in healthy adults, GTS-21 also demonstrated cognitive enhancement across all doses, with a statistically significant improvement in attention related and memory related tasks (Kitagawa, et al. Neuropsychopharmacology (2003), 28, 542-551).
Synonyms
  • 3-(2,4-dimethoxybenzylidene)anabaseine
  • DMXB-A
  • DMXB-Anabaseine
  • Dimethoxybenzylidene anabaseine
  • GTS-21
IndicationInvestigated for use/treatment in alzheimer's disease and schizophrenia and schizoaffective disorders.
Categories
  • Benzene Derivatives
  • Cholinergic Agents
  • Cholinergic Agonists
  • Cytochrome P-450 CYP1A2 Substrates
  • Cytochrome P-450 CYP2E1 Substrates
CAS number148372-04-7

Drug Targets

NameTarget SequencePharmacological ActionActions
Neuronal acetylcholine receptor subunit alpha-7MRCSPGGVWLALAASLLHVSLQGEFQRKLYKELVKNYNPLERPVANDSQP...unknown
Cytochrome P450 1A2MALSQSVPFSATELLLASAIFCLVFWVLKGLRPRVPKGLKSPPEPWGWPL...unknownsubstrate
Cytochrome P450 2E1MSALGVTVALLVWAAFLLLVSMWRQVHSSWNLPPGPFPLPIIGNLFQLEL...unknownsubstrate
Drug Info/Drug Targets: DrugBank 3.0: a comprehensive resource for 'omics' research on drugs. Knox C, Law V, Jewison T, Liu P, Ly S, Frolkis A, Pon A, Banco K, Mak C, Neveu V, Djoumbou Y, Eisner R, Guo AC, Wishart DS. Nucleic Acids Res. 2011 Jan; 39 (Database issue):D1035-41. | PMID:21059682

Related Resource References

Resource NameReference
Pharos CHEMBL134713
PubChem 5310985
ChEMBL CHEMBL134713