Pazinaclone has a very similar pharmacological profile to the
benzodiazepines including sedative and anxiolytic properties, but with less
amnestic effects,[1] and at low doses it is a relatively selective anxiolytic, with sedative effects only appearing at higher doses.[2]
Pazinaclone produces its sedative and anxiolytic effects by acting as a
partial agonist at
GABAA benzodiazepine receptors, although pazinaclone is more subtype-selective than most benzodiazepines.[3]
Synthesis
Reaction of 2-amino-7-chloro-1,8-
naphthyridine with
phthalic anhydride leads to the corresponding phthalimide. Selective reduction of one of the imide carbonyl groups in essence converts that to an aldehyde. Condensation with tert-butyl(triphenylphosphoranylidene)acetate gives the Wittig product.
The carboxylic acid is then treated with diethyl cyanophosphonate to convert that to an activated acid cyanide; reaction with 1,4-dioxa-8-azaspiro[4.5]decane results in formation of the corresponding amide, pazinaclone.
^Suzuki M, Uchiumi M, Murasaki M (October 1995). "A comparative study of the psychological effects of DN-2327, a partial benzodiazepine agonist, and alprazolam". Psychopharmacology. 121 (4): 442–50.
doi:
10.1007/BF02246492.
PMID8619007.
S2CID35222663.
^Atack JR (May 2005). "The benzodiazepine binding site of GABA(A) receptors as a target for the development of novel anxiolytics". Expert Opinion on Investigational Drugs. 14 (5): 601–18.
doi:
10.1517/13543784.14.5.601.
PMID15926867.
S2CID22793644.