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7-Azaindole derivatives as potential partial nicotinic agonists.

Bioorganic & medicinal chemistry letters (2007-11-17)
Axel R Stoit, Arnold P den Hartog, Harry Mons, Sjoerd van Schaik, Nynke Barkhuijsen, Cees Stroomer, Hein K A C Coolen, Jan Hendrik Reinders, Tiny J P Adolfs, Martina van der Neut, Hiskias Keizer, Chris G Kruse
ABSTRACT

We have investigated a series of 7-azaindoles as potential partial agonists of the alpha4beta2 nicotinic acetylcholine receptor (nAChR). Three series of 7-azaindole derivatives have been synthesized and evaluated for rat brain neuronal nicotinic receptor affinity and functional activity. Compound (+)-51 exhibited the most potent nAChR binding (Ki = 10 nM). Compound 30A demonstrated both moderate binding affinity and partial agonist potency, thus representing a promising lead for the indications of cognition and smoking cessation.

MATERIALS
Product Number
Brand
Product Description

Supelco
(−)-Nicotine solution, 1.0 mg/mL, analytical standard, for drug analysis
Sigma-Aldrich
(−)-Nicotine, ≥99% (GC), liquid
Supelco
(−)-Nicotine, PESTANAL®, analytical standard