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Pazinaclone

Chemical compound

Pazinaclone

Chemical compound

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Pazinaclone (DN-2327) is a sedative and anxiolytic drug in the cyclopyrrolone family of drugs. Some other cyclopyrrolone drugs include zopiclone and eszopiclone.

Pazinaclone has a very similar pharmacological profile to the benzodiazepines including sedative and anxiolytic properties, but with less amnestic effects, and at low doses it is a relatively selective anxiolytic, with sedative effects only appearing at higher doses.

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.

Synthesis

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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.

References

References

  1. (March 1992). "Effect of a new anxiolytic, DN-2327, on learning and memory in rats". Pharmacology, Biochemistry, and Behavior.
  2. (October 1995). "A comparative study of the psychological effects of DN-2327, a partial benzodiazepine agonist, and alprazolam". Psychopharmacology.
  3. (May 2005). "The benzodiazepine binding site of GABA(A) receptors as a target for the development of novel anxiolytics". Expert Opinion on Investigational Drugs.
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cyclopyrrolones sedatives isoindolines lactams acetamides naphthyridines gabaa-receptor-positive-allosteric-modulators
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