Pazinaclone
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| Formula | C25H23ClN4O4 |
| Molar mass | 478.93g·mol−1 |
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Pazinaclone(DN-2327) is asedativeandanxiolyticdrug in thecyclopyrrolonefamily of drugs. Some other cyclopyrrolone drugs includezopicloneandeszopiclone.
Pazinaclone has a very similar pharmacological profile to thebenzodiazepinesincluding sedative and anxiolytic properties, but with lessamnesticeffects,[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 apartial agonistatGABAAbenzodiazepine receptors, although pazinaclone is more subtype-selective than most benzodiazepines.[3]
Synthesis[edit]
Reaction of 2-amino-7-chloro-1,8-naphthyridinewithphthalic anhydrideleads to the corresponding phthalimide. Selective reduction of one of the imide carbonyl groups in essence converts that to an aldehyde. Condensation withtert-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.
See also[edit]
References[edit]
- ^Wada T, Fukuda N (March 1992). "Effect of a new anxiolytic, DN-2327, on learning and memory in rats".Pharmacology, Biochemistry, and Behavior.41(3): 573–9.doi:10.1016/0091-3057(92)90375-p.PMID1350101.S2CID20581568.
- ^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.