Tetrakis-azaaromatic quaternary ammonium salts: Novel subtype-selective antagonists at neuronal nicotinic receptors that mediate nicotine-evoked dopamine release

Bioorganic and Medicinal Chemistry Letters

Volumn 18, Issue 21, 2008, Pages 5753-5757

  Zhang, Zhenfa ^a   Zheng, Guangrong ^a   Pivavarchyk, Marharyta ^a   Deaciuc, A Gabriela ^a   Dwoskin, Linda P ^a   Crooks, Peter A ^a  

^a University of Kentucky   (United States)

Author keywords

Dopamine release; Nicotine addiction; Nicotinic acetylcholine receptor; Quaternary ammonium

Indexed keywords

AROMATIC COMPOUND; DOPAMINE; HETEROCYCLIC COMPOUND; NICOTINE; NICOTINIC RECEPTOR; NICOTINIC RECEPTOR BLOCKING AGENT; RECEPTOR SUBTYPE;

ANIMAL TISSUE; ARTICLE; BRAIN SLICE; CONTROLLED STUDY; CORPUS STRIATUM; DOPAMINE RELEASE; DRUG POTENCY; DRUG RECEPTOR BINDING; DRUG SELECTIVITY; DRUG SYNTHESIS; IC 50; NONHUMAN; RAT; RECEPTOR AFFINITY; STRUCTURE ACTIVITY RELATION;

AZA COMPOUNDS; DOPAMINE; NEURONS; NICOTINE; NICOTINIC ANTAGONISTS; QUATERNARY AMMONIUM COMPOUNDS; SALTS;

EID: 54049099101     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmcl.2008.09.084     Document Type: Article

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26. 3+, 369.87, 370.20, 370.53).Compound 11g: A mixture of 5,5′,5′′,5′′′-(1,2,4,5-benzentetrayl )-tetrakis-[1-bromopentane] (10) (330 mg, 0.49 mmol) and 3-(3-hydroxypropanyl)-pyridine (300 mg, 2.3 mmol) was heated at 60-70 °C for 18 h. The resulted mixture was treated with diethyl ether and then dissolved in water (15 mL), the aqueous solution was extracted extensively with chloroform (5× 30 mL). Water was removed through lyophilization to afford 460 mg of the title compound.